GB994640A - Process for the manufacture of ª‡:ª†-disubstituted acetoacetic acid esters - Google Patents
Process for the manufacture of ª‡:ª†-disubstituted acetoacetic acid estersInfo
- Publication number
- GB994640A GB994640A GB3433861A GB3433861A GB994640A GB 994640 A GB994640 A GB 994640A GB 3433861 A GB3433861 A GB 3433861A GB 3433861 A GB3433861 A GB 3433861A GB 994640 A GB994640 A GB 994640A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ene
- acid
- sodium acetate
- disubstituted
- reaction
- 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
Links
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000001632 sodium acetate Substances 0.000 abstract 3
- 235000017281 sodium acetate Nutrition 0.000 abstract 3
- -1 1,3-disubstituted cyclobut-1-ene-2-ol-4-one Chemical class 0.000 abstract 2
- ZSADIOZWRMCYNY-UHFFFAOYSA-N 3-hydroxy-2,4-dimethylcyclobut-2-en-1-one Chemical compound CC1C(O)=C(C)C1=O ZSADIOZWRMCYNY-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 abstract 2
- DYKOGWMQOXNHDP-UHFFFAOYSA-N 2,4-diethyl-3-hydroxycyclobut-2-en-1-one Chemical compound CCC1C(O)=C(CC)C1=O DYKOGWMQOXNHDP-UHFFFAOYSA-N 0.000 abstract 1
- ZCVPGCZVSRAPQW-UHFFFAOYSA-N 3-hydroxy-2,4-di(propan-2-yl)cyclobut-2-en-1-one Chemical compound CC(C)C1C(O)=C(C(C)C)C1=O ZCVPGCZVSRAPQW-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- KKSAZXGYGLKVSV-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO KKSAZXGYGLKVSV-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- C07C69/72—Acetoacetic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
a ,g -Disubstituted acetoacetic acid esters are prepared by reaction between a 1,3-disubstituted cyclobut-1-ene-2-ol-4-one of the general formula <FORM:0994640/C2/1> wherein R is an alkyl radical, and an alkanol. The reaction may be carried out in the presence or absence of an esterification or transesterification catalyst, several classes of which are mentioned, and the reaction mixture may be heated. In examples the following compounds are prepared: (1) a ,g -dimethylacetoacetic acid butyl ester from butanol and 1,3-dimethylcyclobut - 1 - ene - 2 - ol - 4 - one; (2) a ,g - dimethylacetoacetic acid ethyl ester from ethanol and 1,3 - dimethylcyclobut - 1 - ene - 2 - ol-4-one in the presence of sodium acetate, sodium ethoxide, titanium tetrabutylate, concentrated sulphuric acid or boron trifluoride as catalyst; (3) a ,g -diisopropylacetoacetic acid ethyl ester from ethanol and 1,3-diisopropylcyclobut-1-ene-2 - ol - 4 - one in the presence of sodium acetate; (14) a ,g -diethylacetoacetic acid isoamyl ester from isoamyl alcohol and 1,3-diethylcyclobut-1-ene-2-ol-4-one in the presence of sodium acetate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEW28618A DE1265735B (en) | 1960-09-23 | 1960-09-23 | Process for the preparation of alpha, gamma-di- (alkyl) -acetoacetic esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB994640A true GB994640A (en) | 1965-06-10 |
Family
ID=7598988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3433861A Expired GB994640A (en) | 1960-09-23 | 1961-09-25 | Process for the manufacture of ª‡:ª†-disubstituted acetoacetic acid esters |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE608424A (en) |
| CH (1) | CH404633A (en) |
| DE (1) | DE1265735B (en) |
| GB (1) | GB994640A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146724A (en) * | 1975-12-24 | 1979-03-27 | Basf Aktiengesellschaft | Process for the manufacture of isopropyl 4-methylimidazole-5-carboxylate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2167168A (en) * | 1936-07-17 | 1939-07-25 | Carbide & Carbon Chem Corp | Preparation of acetoacetic esters of aliphatic alcohols |
| US2228452A (en) * | 1937-04-01 | 1941-01-14 | Standard Oil Dev Co | Preparation of esters |
| US2351366A (en) * | 1939-07-03 | 1944-06-13 | Pohl Franz Josef | Process of preparing acetoacetic esters |
| DE974554C (en) * | 1952-01-12 | 1961-02-09 | Wacker Chemie Gmbh | Process for the production of acetoacetic esters |
-
1960
- 1960-09-23 DE DEW28618A patent/DE1265735B/en active Pending
-
1961
- 1961-09-21 CH CH1099361A patent/CH404633A/en unknown
- 1961-09-22 BE BE608424A patent/BE608424A/en unknown
- 1961-09-25 GB GB3433861A patent/GB994640A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4146724A (en) * | 1975-12-24 | 1979-03-27 | Basf Aktiengesellschaft | Process for the manufacture of isopropyl 4-methylimidazole-5-carboxylate |
Also Published As
| Publication number | Publication date |
|---|---|
| CH404633A (en) | 1965-12-31 |
| BE608424A (en) | 1962-03-22 |
| DE1265735B (en) | 1968-04-11 |
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