US2030423A - Alkyl resorcinols - Google Patents
Alkyl resorcinols Download PDFInfo
- Publication number
- US2030423A US2030423A US682270A US68227033A US2030423A US 2030423 A US2030423 A US 2030423A US 682270 A US682270 A US 682270A US 68227033 A US68227033 A US 68227033A US 2030423 A US2030423 A US 2030423A
- Authority
- US
- United States
- Prior art keywords
- alkyl
- resorcinol
- resorcinols
- carbon
- alkyl resorcinols
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229930188104 Alkylresorcinol Natural products 0.000 title description 10
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical group CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- HHSCZZZCAYSVRK-UHFFFAOYSA-N 2-octylbenzene-1,3-diol Chemical group CCCCCCCCC1=C(O)C=CC=C1O HHSCZZZCAYSVRK-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- PFPZRMUCMKVUEX-UHFFFAOYSA-N 4-heptylbenzene-1,3-diol Chemical group CCCCCCCC1=CC=C(O)C=C1O PFPZRMUCMKVUEX-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical group CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- 101100028482 Caenorhabditis elegans pal-1 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- -1 Hep tyl resorcinols Chemical class 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
Definitions
- This invention relates to new higher alkyl resorcinols characterized by the fact that the alkyl group is attached to the resorcinol nucleus by a carbon other than an end carbon and contains not less than seven carbon atoms.
- the compounds may be represented by the general formula C6H3(OH)2(CR1R2R3) in which R1 may be hydrogen or an alkyl and R2 and R3 are alkyl groups, either straight chain or branched, the group (CR1R2R3) containing not less than seven carbon atoms.
- the compounds within the scope of this invention are the heptyl, the octyl and the nonyl derivatives of resorcinol.
- the new alkyl resorcinols may be prepared very efficiently, simply and comparatively cheaply by the condensation of resorcinol with an alcohol or alkyl halide having the desired number and arrangement of carbon atoms.
- the new alkyl resorcinols are characterized by special germicidal and antiseptic properties combined with practical non-toxicity. They may be incorporated in various solutions, jellies, lozenges or other vehicles in proportions ranging up to five parts of the alkyl resorcinol for one thousand parts of the medium, and in special preparations for internal administration they may be used in higher concentrations ranging up to full strength.
- Secondary octyl resorcinol may be prepared by the process described in the following example: A mixture of g. of resorcinol, 25 g. of secondary octanol (methyl n-hexyl carbinol, CH3CHOHCH2CH2CI-I2CH2CH2CH3), and 10 g. of zinc chloride is heated to C. until water distills off. More of the octanol is added slowly at such rate as to correspond to the water distilling off. The oil which comes off with the waterisconstantly returned to the reaction mixture by means of a water separator. After a total of 80 gr. of the octanol has been added, the reaction is allowed to continue for one hour, after which the temperature is raised to 200 C. when heating is stopped. The resulting oil is washed with water and distilled, the fraction boiling at -210 C.
- the distillate is a colorless to pale yellow oil.
- Secondary heptyl resorcinol may be prepared by the process described in the following example: 22 g. resorcinol, 36 g. secondary heptyl bromide (CI-I3CI-I2CH2CHBICH2CH2CH3) and 5 g. anhydrous zinc chloride are mixed and heated while stirring to 130 C. until no further evolution of gas takes place. The mixture is allowed to cool, taken up with toluol, and washed several times with water, then it is distilled in vacuo. The distillate is redistilled and the fraction boiling at 1'75-190 C. (3 mm.) is collected.
- Secondary heptyl resorcinol having the formula CHOHICHI CHQuH3(QH)3 5.
- Secondary octyl resorcinol having the formula omomomcmom mula CHzCHzCHzCH:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Patented Feb. 11, 1936 UNITED STATES ALKYL RESORCINOLS William E. Austin, New York, N. 'Y., assignor to Bank of The Manhattan Company No Drawing. Application July 26, 1933, Serial No. 682,270
6 Claims.
This invention relates to new higher alkyl resorcinols characterized by the fact that the alkyl group is attached to the resorcinol nucleus by a carbon other than an end carbon and contains not less than seven carbon atoms.
The compounds may be represented by the general formula C6H3(OH)2(CR1R2R3) in which R1 may be hydrogen or an alkyl and R2 and R3 are alkyl groups, either straight chain or branched, the group (CR1R2R3) containing not less than seven carbon atoms.
Among the compounds within the scope of this invention are the heptyl, the octyl and the nonyl derivatives of resorcinol.
The usual method for preparing alkyl resorcinols, namely treating resorcinol with a fatty acid, fatty acid chloride or fatty acid anhydride in the presence of a condensing agent, and then reducing the resulting ketone produces only primary alkyl resorcinols. The compounds of the present invention cannot be obtained by this procedure.
The new alkyl resorcinols may be prepared very efficiently, simply and comparatively cheaply by the condensation of resorcinol with an alcohol or alkyl halide having the desired number and arrangement of carbon atoms.
The new alkyl resorcinols are characterized by special germicidal and antiseptic properties combined with practical non-toxicity. They may be incorporated in various solutions, jellies, lozenges or other vehicles in proportions ranging up to five parts of the alkyl resorcinol for one thousand parts of the medium, and in special preparations for internal administration they may be used in higher concentrations ranging up to full strength.
Secondary octyl resorcinol may be prepared by the process described in the following example: A mixture of g. of resorcinol, 25 g. of secondary octanol (methyl n-hexyl carbinol, CH3CHOHCH2CH2CI-I2CH2CH2CH3), and 10 g. of zinc chloride is heated to C. until water distills off. More of the octanol is added slowly at such rate as to correspond to the water distilling off. The oil which comes off with the waterisconstantly returned to the reaction mixture by means of a water separator. After a total of 80 gr. of the octanol has been added, the reaction is allowed to continue for one hour, after which the temperature is raised to 200 C. when heating is stopped. The resulting oil is washed with water and distilled, the fraction boiling at -210 C.
(3 mm.) being collected. The distillate is a colorless to pale yellow oil.
Secondary heptyl resorcinol may be prepared by the process described in the following example: 22 g. resorcinol, 36 g. secondary heptyl bromide (CI-I3CI-I2CH2CHBICH2CH2CH3) and 5 g. anhydrous zinc chloride are mixed and heated while stirring to 130 C. until no further evolution of gas takes place. The mixture is allowed to cool, taken up with toluol, and washed several times with water, then it is distilled in vacuo. The distillate is redistilled and the fraction boiling at 1'75-190 C. (3 mm.) is collected.
It is to be understood that the foregoing emb'odiments are merely illustrative and .by no means limitative of the invention which may assume various-other formsas to the procedures and as to the particular alkyl resorcinols prepared-within the scope of the appended claims.
I claim:
1. Alkyl resorcinols of the general formula CeH3(OH)2(CHR1R2) where H is hydrogen, and R1 and R2 are alkyls, the group (CI-IRaRz) containing not less than seven carbon atoms, and being attached to the resorcinol nucleus by a carbon other than an end carbon.
2. Hep tyl resorcinols in which the alkyl is a secondary heptyl group attached to the resorcinol nucleus by a carbon other than an end carbon.
3. Octyl resorcinols in which the alkyl is a secondary octyl group attached to the resorcinol nucleus by a carbon other than an end carbon.
4. Secondary heptyl resorcinol having the formula CHOHICHI CHQuH3(QH)3 5. Secondary octyl resorcinol having the formula omomomomcmom mula CHzCHzCHzCH:
CH-CQH3(OH)I CHzCHzCHzOHI WILLIAM E. AUSTIN.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US682270A US2030423A (en) | 1933-07-26 | 1933-07-26 | Alkyl resorcinols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US682270A US2030423A (en) | 1933-07-26 | 1933-07-26 | Alkyl resorcinols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2030423A true US2030423A (en) | 1936-02-11 |
Family
ID=24738956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US682270A Expired - Lifetime US2030423A (en) | 1933-07-26 | 1933-07-26 | Alkyl resorcinols |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2030423A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439421A (en) * | 1944-08-04 | 1948-04-13 | Mathieson Alkali Works Inc | Process for the production of dialkylated polyhydric phenols |
| US2509386A (en) * | 1950-05-30 | Debenzopyran marihuana-like | ||
| US2839570A (en) * | 1953-08-12 | 1958-06-17 | Hoffmann La Roche | Process for the production of 1-acyloxy-2-methyl-3-phytyl-4-hydroxy naphtalenes |
| US4093667A (en) * | 1977-03-14 | 1978-06-06 | Continental Oil Company | Preparation of 4-n-hexylresorcinol |
| WO2004052814A1 (en) * | 2002-12-09 | 2004-06-24 | Unilever Plc | Process for the preparation of a cosmetic active |
-
1933
- 1933-07-26 US US682270A patent/US2030423A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2509386A (en) * | 1950-05-30 | Debenzopyran marihuana-like | ||
| US2439421A (en) * | 1944-08-04 | 1948-04-13 | Mathieson Alkali Works Inc | Process for the production of dialkylated polyhydric phenols |
| US2839570A (en) * | 1953-08-12 | 1958-06-17 | Hoffmann La Roche | Process for the production of 1-acyloxy-2-methyl-3-phytyl-4-hydroxy naphtalenes |
| US4093667A (en) * | 1977-03-14 | 1978-06-06 | Continental Oil Company | Preparation of 4-n-hexylresorcinol |
| WO2004052814A1 (en) * | 2002-12-09 | 2004-06-24 | Unilever Plc | Process for the preparation of a cosmetic active |
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