JPH0952860A - Production of hydroxyphenyl benzyl ketones - Google Patents

Abstract

PROBLEM TO BE SOLVED: To easily obtain the subject compound useful as an intermediate important as a raw material for metal extractants, feed additives and pharmaceuticals in high yield at a low cost. SOLUTION: The objective hydroxyphenyl benzyl ketone compound is expressed by formula I (R1 and R2 are each a halogen, hydroxy, etc.; R3 and R4 are each H, an alkyl, etc.), e.g. 2,4-dihydroxyphenyl benzyl ketone. The compound of formula I can be produced by dispersing a phenolic compound of formula II preferably' in 3-7 times amount (cc/g) of an aromatic hydrocarbon such as toluene, adding 0.90-1.1 times mol of anhydrous aluminum chloride to the dispersion preferably at 20-30 deg.C, stirring for 1-3hr at the above temperature to dissolve the anhydrous aluminum chloride, dropping 0.9-1.1 times mol of a phenylacetyl chloride compound of formula III (e.g. phenylacetyl chloride) to the solution preferably at 5-40 deg.C preferably spending 1-10hr optionally in a form dissolved in an organic solvent and reacting the components for 0.1-5hr.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a method for producing an intermediate. More specifically, it relates to a method for producing hydroxyphenyl benzyl ketones.

[0002]

BACKGROUND OF THE INVENTION Hydroxyphenyl benzyl ketones are used as metal extractants, feed additives, and raw materials for medicines.
It is an important intermediate. As a method for producing the compound,
a) Method of reacting resorcinol and phenylacetonitrile in ether with zinc chloride as a catalyst through hydrochloric acid gas to give ketimine, and then hydrolyzing to give ketone (JP-A-49-1332039), b) resorcinol and phenyl A method of reacting acetic acid with zinc chloride as a catalyst in the absence of a solvent at 120 ° C. for 2.5 hours (Proc.
ndian Acad. Sci. Sect. A, 25
(1947) 322), c) a method of reacting resorcinol and phenylacetic acid chloride in dichloroethane with anhydrous aluminum chloride as a catalyst (Table 5-50079).
7), d) resorcinol and phenylacetic acid chloride in nitrobenzene, using anhydrous aluminum chloride as a catalyst,
Method of reacting (Proc.-Indian Acad.
Sci. Sect. A, 25 (1947) 322) and the like are known. The method a) uses diethyl ether as a solvent, so there is a risk of explosion and the like.
The reaction time is as long as 2 days, which is not an industrial method.
The method b) has poor reproducibility and is not an industrial method. The method of c) is suspected as a carcinogen, and it uses dichloroethane, which has strict environmental regulations, and it is necessary to purify the reaction product using a solvent such as toluene. It cannot be called an industrial manufacturing method. The method d) uses nitrobenzene, which is highly toxic, has a long reaction time of 2 days, and has a low yield of 60%, which cannot be said to be an industrial production method.

[0003]

As described above, since the conventional synthesis method cannot be manufactured industrially at low cost, an inexpensive manufacturing method has been desired.

[0004]

Means for Solving the Problems The present inventors have conducted various studies on the reaction of phenols and phenylacetyl chlorides using anhydrous aluminum chloride as a catalyst to produce hydroxyphenylbenzyl ketones. By selecting an aromatic hydrocarbon as the solvent, it was found that the side reaction was suppressed and the reaction proceeded smoothly, and the present invention was completed. It is known that an inert solvent such as carbon disulfide, nitrobenzene, dichloromethane or dichloroethane is used as a solvent for the Friedel-Crafts reaction, but there is no example using an aromatic hydrocarbon. This is because aromatic hydrocarbons are believed to undergo the Friedel-Crafts reaction. However, the reaction rate of the phenols is remarkably faster than that of the reaction of the aromatic hydrocarbon used as the solvent, so that the hydroxybenzyl ketones can be obtained in good yield. This fact is surprising, not quite inferrable. Benzene is a carcinogen, but toluene, xylene and the like have low toxicity and are industrially used as organic solvents, and are easy-to-use solvents.
Further, these solvents are suitable not only as a reaction solvent but also as a purification solvent for hydroxybenzyl ketones.

That is, the present invention (1) uses aromatic hydrocarbon as a reaction solvent in a method for producing hydroxyphenylbenzyl ketone by reacting phenols with phenylacetyl chlorides using anhydrous aluminum chloride as a catalyst. (2) A method for producing a hydroxyphenyl benzyl ketone, wherein the aromatic hydrocarbon is toluene, ethylbenzene,
o-xylene, m-xylene, p-xylene, a method for producing a hydroxyphenylbenzyl ketone according to the above (1), which is at least one selected from mesitylene (3) The phenols are represented by the formula (1),

Embedded image (In the formula, R ₁ and R ₂ represent a halogen atom, a hydroxyl group, an alkyl group, an alkoxy group or a hydrogen atom and may be the same or different.) Phenylacetyl chlorides are represented by the formula (2). Is

Embedded image (In the formula, R ₃ and R ₄ represent a hydrogen atom, an alkyl group or an alkoxy group and may be the same or different.) The hydroxyphenylbenzyl ketones are represented by the formula (3). The method for producing a hydroxyphenylbenzyl ketone according to the above (1) or (2), which is a compound

[Chemical 6] (4) The hydroxyphenyl according to the above (1), (2) or (3), wherein the phenols are resorcinol, the phenylacetyl chlorides are phenylacetyl chloride, and the hydroxyphenylbenzyl ketones are 2,4-dihydroxyphenylbenzyl ketone. The present invention relates to a method for producing benzyl ketones.

[0006]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described in detail below.
Specific examples of phenols used in the present invention include resorcinol, hydroquinone, phloroglucinol,
p-cresol, p-chlorophenol, 2,4-dichlorophenol, 2-chloro-4-methylphenol,
2-chlorophenol, 2,6-dihydroxytoluene and the like can be mentioned. Specific examples of phenylacetyl chlorides include phenylacetyl chloride and 3,4-
Examples thereof include dimethylphenyl acetyl chloride and 3,4-diethoxyphenyl acetyl chloride.
Aromatic hydrocarbons are used as the reaction solvent, but 1
Preferred examples thereof include benzenes which may be substituted with one or more alkyl groups or cycloalkyl groups. Specific examples thereof include benzene, toluene, ethylbenzene, cumene, butylbenzene, pentylbenzene, dodecylbenzene and cyclohexylbenzene.
Disubstituted products such as substituted products, xylene, ethyltoluene, propyltoluene, cymene, butyltoluene, ethylisopropylbenzene, diethylbenzene, dipropylbenzene, dipentylbenzene, and tetralin, trimethylbenzene such as hemimellitene, pseudocumene, and mesitylene, triethylbenzene, diethyl. Examples thereof include trisubstituted products such as toluene, dimethylethylbenzene, dimethylpropylbenzene and triisopropylbenzene, and tetrasubstituted products such as tetramethylbenzene such as planitene and isodulene, trimethylisobutylbenzene and tetraethylbenzene. Among these, toluene, ethylbenzene, o-xylene, m-xylene, p-xylene, mesitylene and the like are particularly preferable examples.

The reaction method is as follows.
2 to 30 times (cc / g), preferably 2 to 10 times, particularly preferably 3 to 7 times, dispersed in an aromatic hydrocarbon, and 1
0 to 40 ° C, preferably 20 to 30 ° C, 0.1 to 5 times (molar ratio, relative to phenols), preferably 0.5 to 2
Double, particularly preferably 0.90 to 1.1 times, anhydrous aluminum chloride is added, and the mixture is stirred at the same temperature for 30 minutes to 5 hours, preferably 1 to 3 hours to dissolve the anhydrous aluminum chloride. After dissolution, it is -20 to 100 ° C, preferably 0 to 6
0 ° C., particularly preferably 5 to 40 ° C., 0.5 to 2.0
Times (molar ratio, to phenols), preferably 0.9-
If necessary, a solution prepared by dissolving 1.1 times as much phenylacetyl chloride in the organic solvent as referred to in the present invention is used.
It is added dropwise over a period of minutes to 20 hours, preferably 1 to 10 hours. The reaction may be completed at the same temperature for 0.1 to 5 hours, or the temperature may be increased by 20 to 30 ° C. to shorten the reaction completion time. Also, after phenylacetyl chloride was added dropwise, the mixture was stirred at the same temperature for 0.1 to 5 hours, and then,
The stirring may be stopped and the mixture may be left at the same temperature for 1 to 5 hours, or may be left as it is at room temperature overnight.

In order to take out the target substance from the reaction liquid, for example, the following treatment is carried out. In the reaction solution left to stand, the product complex is
Since it has been precipitated, the organic solvent in the supernatant of the reaction solution is absorbed, and then water is added in an amount of 1 to 30 times (weight ratio, relative to phenols), preferably 5 to 20 times, particularly preferably 7-1.
3 times added, 40 to 100 ° C., preferably 50 to 80
C., particularly preferably 60 to 70.degree. C., holding for 10 minutes to 3 hours, preferably 20 minutes to 2 hours, then at the same temperature,
Alternatively, by lowering the temperature by 10 to 20 ° C, 36% hydrochloric acid is 0.1 to 5 times (weight ratio, to phenols), preferably 0.3 to 3 times, particularly preferably 0.5 to Add 2 times and hold for 10 minutes to 2 hours. Further, a surfactant is added to
1-5% by weight (with respect to phenols), preferably 0.8
~ 2 wt% added, 10 minutes to 2 hours, preferably 15-3
After keeping the same temperature for 0 minutes, it is cooled. It is cooled to 10 to 30 ° C. and the precipitated product crystals are suction filtered. Wash with water until the filtrate is neutral. 50 to filter cake
Dry with hot air at 60 ° C. Examples of the surfactant include anionic surfactants such as alkylbenzene sulfonate, alkylnaphthalene sulfonate, alkyldiphenyl ether disulfonate, and naphthalene sulfonic acid formalin condensate, polyoxyethylene alkyl ether, polyoxyethylene alkyl allyl. Examples thereof include nonionic surfactants such as ethers and polyoxyethylene derivatives. Also, do not absorb the organic solvent,
Water may be added to decompose the complex. That is, the amount of water is not particularly limited, but is 1 to 30 times (weight ratio, relative to phenols), preferably 3 to 20 times, particularly preferably 5 to 1.
3 times added, 40 to 100 ° C., preferably 50 to 80
C., particularly preferably 60 to 70.degree. C., holding for 10 minutes to 3 hours, preferably 20 minutes to 2 hours, then at the same temperature,
Alternatively, by lowering the temperature by 10 to 20 ° C, 36% hydrochloric acid is 0.1 to 5 times (weight ratio, to phenols), preferably 0.3 to 3 times, particularly preferably 0.5 to Add 2 times and hold for 10 minutes to 2 hours. After decomposing the complex, let it stand,
The aqueous layer is separated, water is further added, and the organic solvent layer is washed. Continue washing until the pH of the aqueous layer is around 7. The washed organic solvent layer is used as it is or concentrated to precipitate crystals, which are then filtered under reduced pressure. The filter cake is washed with the same solvent and dried in the same manner as above to obtain hydroxyphenylbenzyl ketones.

[0009]

EXAMPLES The present invention will be described more specifically with reference to examples, but the present invention is not limited to only these examples.

Example 1 A 1000 cc 4-neck flask equipped with a stirrer, a thermometer, a calcium chloride tube, and a reflux condenser was charged with 250 c of toluene.
c, 55 g of resorcinol were added, dispersed and suspended, and 2
Hold at 0-25 ° C. Next, anhydrous aluminum chloride 67
g was added, and the mixture was stirred at the same temperature for 2.5 hours. After confirming that aluminum chloride was dissolved, the mixture was cooled with ice water and the contents were kept at 0 to 5 ° C. While maintaining the same temperature there,
Phenylacetyl chloride 77.5g and toluene 1
The mixed solution obtained from 00 cc was added dropwise over 2 hours. After the completion of dropping, the mixture was further stirred at the same temperature for 4 hours and kept at the same temperature for 3.5 hours after the stirring was stopped. Then, the mixture was allowed to stand at room temperature overnight, and toluene in the supernatant of the reaction solution was sucked up. Water 60
After adding 0 cc and holding at 65 to 70 ° C. for 15 minutes, 50 cc of 36% hydrochloric acid was added and holding for 15 minutes, Perex SS-H
(Trade name, anionic surfactant, manufactured by Kao Corporation) 1
After cc was added and the mixture was kept at the same temperature for 15 minutes, it was cooled to room temperature over about 1 hour. After holding at room temperature for about 1 hour, suction filtration was performed. It was washed with about 3000 cc of water. 203 g of filter cake was dried with hot air at 50-60 ° C. for 2 days,
4-dihydroxyphenyl benzyl ketone 94.6 g
I got Yield 83.0% Melting point 112-113 ° C

Example 2 To a 1000 cc 4-neck flask equipped with a stirrer, thermometer, calcium chloride tube, and reflux condenser, toluene 250 c
c, resorcinolorolog was added, dispersed and suspended, and 2
Hold at 0-25 ° C. Next, anhydrous aluminum chloride 67
g was added, and the mixture was stirred at the same temperature for 2.5 hours. After confirming that the aluminum chloride was dissolved, a mixed solution of 77.5 g of phenylacetyl chloride and 100 cc of toluene was added dropwise at the same temperature over 2 hours. After the dropping, the mixture was further stirred at the same temperature for 4 hours and then left overnight at room temperature, and toluene in the supernatant of the reaction solution was absorbed. After adding 600 cc of water and holding at 65 to 70 ° C for 15 minutes, cooling to 50 ° C,
After adding 50 cc of 36% hydrochloric acid and holding at 60 to 65 ° C. for 15 minutes, Perex SS-H 1 cc was added, further holding at the same temperature for 15 minutes, and then cooled to room temperature over about 1 hour. After holding at room temperature for about 1 hour, suction filtration was performed. It was washed with about 3000 cc of water. 50-60 of 144 g of filter cake
It was dried in hot air at 2 ° C. for 2 days to obtain 97.8 g of 2,4-dihydroxyphenylbenzyl ketone. Yield 85.8%
Melting point 112-113 ° C

Example 3 A 1000 cc 4-necked flask equipped with a stirrer, a thermometer, a calcium chloride tube, and a reflux condenser was charged with 250 c of toluene.
c, 55 g of resorcinol were added, dispersed and suspended, and 2
Hold at 0-25 ° C. Next, anhydrous aluminum chloride 67
g was added, and the mixture was stirred at the same temperature for 2.5 hours. After confirming that the aluminum chloride was dissolved, the reaction solution was heated at 38 to 42 ° C.
While holding at 77.5 g of phenylacetyl chloride
And a mixed liquid obtained from 100 cc of toluene were added dropwise over 2.5 hours. After the dropping, the mixture was further stirred at the same temperature for 2 hours and then left overnight at room temperature, and toluene in the supernatant of the reaction solution was sucked up. Add 600 cc of water and add 15 at 65-70 ° C.
After holding for 30 minutes, after cooling to 50 ° C., 50 cc of 36% hydrochloric acid was added, and after holding at 60 to 65 ° C. for 15 minutes, Perex SS-H
After 1 cc was added and the mixture was kept at the same temperature for 15 minutes, it was cooled to room temperature over about 1 hour. After holding at room temperature for about 1 hour, suction filtration was performed. It was washed with about 3000 cc of water. 144 g of filter cake is dried with hot air at 50-60 ° C. for 2 days,
2,4-dihydroxyphenyl benzyl ketone 97.
8 g was obtained. Yield 85.8% Melting point 112-113
° C

Example 4 A 1000 cc 4-neck flask equipped with a stirrer, a thermometer, a calcium chloride tube, and a reflux condenser was charged with 250 c of toluene.
c, 55 g of resorcinol were added, dispersed and suspended, and 2
Hold at 0-25 ° C. Next, anhydrous aluminum chloride 67
g was added, and the mixture was stirred at the same temperature for 2.5 hours. After confirming that the aluminum chloride was dissolved, the reaction solution was heated at 38 to 42 ° C.
While holding at 77.5 g of phenylacetyl chloride
And a mixed liquid obtained from 100 cc of toluene were added dropwise over 2.5 hours. After the dropping, the mixture was further stirred at the same temperature for 4 hours, then left standing at room temperature overnight, and then added with 300 cc of water, and then added to 65 to 7
Hold at 0 ℃ for 15 minutes, cool to 50 ℃, and add 50% 36% hydrochloric acid.
cc was added, and the mixture was kept at 60 to 65 ° C for 15 minutes and then cooled to 50 ° C. Transfer to a 1000 cc separating funnel, let stand for 10 minutes, and extract the lower aqueous layer. 50 ° C warm water 100
The toluene layer was washed 3 times with cc. The toluene layer was concentrated with a reduced pressure rotary evaporator. Crystals were precipitated.
After filtration under reduced pressure, the cake was washed with 100 cc of toluene. The cake was dried with hot air at 50-60 ° C to obtain 91.2 g of 2,4-dihydroxyphenylbenzyl ketone.
Yield 80.0% Melting point 114-115 ° C

Example 5 To a 1000 cc four-necked flask equipped with a stirrer, a thermometer, a calcium chloride tube, and a reflux condenser, toluene 250 c was added.
c, 55 g of resorcinol were added, dispersed and suspended, and 2
Hold at 0-25 ° C. Next, anhydrous aluminum chloride 6
3.5 g was added, and the mixture was stirred at the same temperature for 2.5 hours. After confirming that aluminum chloride was dissolved, hold 77.5 g of phenylacetyl chloride while maintaining the reaction solution at the same temperature.
And a mixed solution obtained from 100 cc of toluene were added dropwise over 2 hours. After the dropping, the mixture was further stirred at the same temperature for 4 hours and then left overnight at room temperature, and toluene in the supernatant of the reaction solution was absorbed. Add 600 cc of water, hold at 65-70 ° C for 15 minutes, cool to 50 ° C, add 50 cc of 36% hydrochloric acid,
After holding at 60-65 ° C for 15 minutes, Perex SS-H 1
After cc was added and the mixture was kept at the same temperature for 15 minutes, it was cooled to room temperature over about 1 hour. After holding at room temperature for about 1 hour, suction filtration was performed. It was washed with about 3000 cc of water. 144 g of filter cake was dried with hot air at 50-60 ° C for 2 days,
4-dihydroxyphenyl benzyl ketone 100.3
g was obtained. Yield 88.0% Melting point 112-113 ° C

Example 6 A 1000 cc four-necked flask equipped with a stirrer, a thermometer, a calcium chloride tube, and a reflux condenser was charged with 250 c of toluene.
c, 2-chlorophenol 64.3g was added and dispersed,
Suspended and kept at 20-25 ° C. Next, 67 g of anhydrous aluminum chloride was added at the same temperature, and the mixture was stirred for 2.5 hours. It was confirmed that aluminum chloride was dissolved, and a mixed solution obtained from 77.5 g of phenylacetyl chloride and 100 cc of toluene was added dropwise at the same temperature over 2.5 hours. After the dropping, the mixture was further stirred at the same temperature for 5 hours and then left overnight at room temperature, and toluene in the supernatant of the reaction solution was absorbed. After adding 600 cc of water and holding at 65 to 70 ° C. for 30 minutes, cooling to 50 ° C., adding 50 cc of 36% hydrochloric acid to 55
After holding at -60 ° C for 15 minutes, Perex SS-H 1cc
Was added, and the mixture was kept at the same temperature for 15 minutes, and then cooled to room temperature over about 1 hour. After holding at room temperature for about 1 hour, suction filtration was performed. It was washed with about 3000 cc of water. 144 g of filter cake was dried under vacuum at 30-40 ° C. for 2 days to give 2-hydroxy-3-chlorophenylbenzyl ketone 10.
5.0 g were obtained. Yield 85.2% Melting point 64-65 ° C

Example 7 A 1000 cc 4-neck flask equipped with a stirrer, a thermometer, a calcium chloride tube, and a reflux condenser was charged with 250 c of toluene.
c, 55 g of hydroquinone were added, dispersed and suspended,
It was kept at 20 to 25 ° C. Next, anhydrous aluminum chloride 6
7 g was added and stirred for 2.5 hours. It was confirmed that aluminum chloride was dissolved, and a mixed solution of 77.5 g of phenylacetyl chloride and 100 cc of toluene was added dropwise at the same temperature over 2.5 hours. After the dropping, the mixture was further stirred at the same temperature for 5 hours and then left overnight at room temperature, and toluene in the supernatant of the reaction solution was absorbed. Add 600 cc of water,
After holding at 70-80 ° C for 30 minutes, 50 cc of 36% hydrochloric acid was added, and after holding at the same temperature for 15 minutes, Perex SS-H 1c
c was added, the mixture was kept at the same temperature for 15 minutes, and then cooled to room temperature over about 1 hour. After holding at room temperature for about 1 hour, suction filtration was performed. It was washed with about 3000 cc of water. Vacuum dry 144 g of filter cake at 50-60 ° C. for 2 days,
96.9 g of dihydroxyphenyl benzyl ketone were obtained. Yield 85% Melting point 120-122 ° C

Example 8 To a 1000 cc four-necked flask equipped with a stirrer, a thermometer, a calcium chloride tube, and a reflux condenser, toluene 250 c
c, 55 g of resorcinol was added, dispersed and suspended,
It was kept at 20 to 25 ° C. Next, anhydrous aluminum chloride 6
7 g was added and stirred for 2.5 hours. It was confirmed that aluminum chloride was dissolved, and at the same temperature, 91.3 g of 3,4-dimethylphenylacetyl chloride and toluene 10
The mixed solution obtained from 0 cc was added dropwise over 2.5 hours.
After the dropping, the mixture was further stirred at the same temperature for 5 hours and then left overnight at room temperature, and toluene in the supernatant of the reaction solution was absorbed. water
After adding 600 cc and holding at 95-100 ° C for 30 minutes, 3
6% hydrochloric acid (50 cc) was added, the mixture was kept at the same temperature for 15 minutes, Perex SS-H 1 cc was added, the mixture was further kept at the same temperature for 15 minutes, and then cooled to room temperature over about 1 hour. After holding at room temperature for about 1 hour, suction filtration was performed. It was washed with about 3000 cc of water. 167 g of filter cake was vacuum dried at 50-60 ° C. for 2 days to give 2,4-dihydroxyphenyl-3,4.
108.8 g of dimethylbenzyl ketone was obtained. Yield 85% Melting point 171-173 ° C

Example 9 A 1000 cc 4-neck flask equipped with a stirrer, a thermometer, a calcium chloride tube, and a reflux condenser was charged with 250 c of toluene.
c, 55 g of resorcinol was added, dispersed and suspended,
It was kept at 20 to 25 ° C. Next, anhydrous aluminum chloride 6
7 g was added and stirred for 2.5 hours. It was confirmed that aluminum chloride was dissolved, and 121.3 g of 3,4-diethoxyphenylacetyl chloride and toluene were added at the same temperature.
The mixed liquid obtained from 100 cc was added dropwise over 2.5 hours. After the dropping, the mixture was further stirred at the same temperature for 5 hours and then left overnight at room temperature, and toluene in the supernatant of the reaction solution was absorbed.
Add 600 cc of water and hold at 95-100 ° C for 30 minutes, add 50 cc of 36% hydrochloric acid, hold for 15 minutes at the same temperature, add Perex SS-H 1 cc, hold for 15 minutes at the same temperature, and then for about 1 hour. It cooled over time to room temperature. After holding at room temperature for about 1 hour, suction filtration was performed. It was washed with about 3000 cc of water. 192g of filter cake 50-60
It was vacuum dried at 2 ° C. for 2 days to obtain 134.3 g of 2,4-dihydroxyphenyl-3,4-diethoxybenzyl ketone. Yield 85% Melting point 141-143 ° C

Example 10 A 1000 cc 4-necked flask equipped with a stirrer, a thermometer, a calcium chloride tube, and a reflux condenser was charged with 250 c of toluene.
c, 63 g of phloroglucinol were added, dispersed and suspended, and maintained at 20 to 25 ° C. Next, 67 g of anhydrous aluminum chloride was added and stirred for 2.5 hours. After confirming that the aluminum chloride has dissolved, cool it with ice water and
It was kept at 5 ° C. A mixed solution obtained from 77.5 g of phenylacetyl chloride and 100 cc of toluene was added dropwise thereto at the same temperature over 2 hours. After the dropping, the mixture was further stirred at the same temperature for 1 hour and kept at the same temperature for 3.5 hours after the stirring was stopped. Then, the mixture was allowed to stand at room temperature overnight, and toluene in the supernatant of the reaction solution was sucked up. Add 600 cc of water, 60 ~
After holding at 65 ° C. for 30 minutes, 50 cc of 36% hydrochloric acid was added, after holding at the same temperature for 15 minutes, Perex SS-H 1 cc was added, further holding at the same temperature for 15 minutes, and then cooled to room temperature over about 1 hour. After holding at room temperature for about 1 hour, suction filtration was performed. It was washed with about 3000 cc of water. 203 g of filter cake was dried with hot air at 50-60 ° C. for 2 days to give 2,4,6-
Trihydroxyphenyl benzyl ketone 103.7g
I got Yield 85.0% Melting point 117-120 ° C

[0020]

EFFECTS OF THE INVENTION Hydroxyphenylbenzyl ketones can be obtained in a high yield by simple operations and by using raw materials with low toxicity.

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Claims (4)

[Claims] 1. A method for producing hydroxyphenylbenzyl ketones by reacting phenols with phenylacetyl chlorides using anhydrous aluminum chloride as a catalyst, wherein an aromatic hydrocarbon is used as a reaction solvent. Method for producing phenyl benzyl ketones. 2. The aromatic hydrocarbon is at least one selected from toluene, ethylbenzene, o-xylene, m-xylene, p-xylene and mesitylene.
A method for producing the hydroxyphenyl benzyl ketones described. 3. A phenol is represented by the formula (1): (In the formula, R ₁ and R ₂ represent a halogen atom, a hydroxyl group, an alkyl group, an alkoxy group or a hydrogen atom and may be the same or different.) Phenylacetyl chlorides are represented by the formula (2). And then (In the formula, R ₃ and R ₄ represent a hydrogen atom, an alkyl group or an alkoxy group and may be the same or different.) The hydroxyphenylbenzyl ketones are represented by the formula (3). The method for producing hydroxyphenyl benzyl ketones according to claim 1 or 2, which is a compound. Embedded image 4. The phenol, resorcinol, phenylacetyl chloride, phenylacetyl chloride, and hydroxyphenylbenzyl ketones, 2,4-dihydroxyphenylbenzyl ketone.
A method for producing the hydroxyphenyl benzyl ketones described.