GB830637A - A process for the preparation of azelaic acid semi-ester suitable for making civetone dicarboxylic acid - Google Patents
A process for the preparation of azelaic acid semi-ester suitable for making civetone dicarboxylic acidInfo
- Publication number
- GB830637A GB830637A GB1141758A GB1141758A GB830637A GB 830637 A GB830637 A GB 830637A GB 1141758 A GB1141758 A GB 1141758A GB 1141758 A GB1141758 A GB 1141758A GB 830637 A GB830637 A GB 830637A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ester
- civetone
- azelaic
- give
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/10—Polyhydroxy carboxylic acids
- C07C59/105—Polyhydroxy carboxylic acids having five or more carbon atoms, e.g. aldonic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Azelaic acid semiester is prepared by oxidizing a dihydroxy-stearic acid ester to a semialdehyde ester of azelaic acid by mixing and stirring a solution of the ester in a watersoluble organic solvent, such as methyl or ethyl alcohol, with an alpha-beta glycol rupturing agent such as sodium metaperiodate, followered by distillation, and oxidizing the semialdehyde ester thus obtained to azelaic acid semiester by treating an acetone solution of the semi-aldehyde ester with an aqueous solution of potassium permanganate in the presence of an acid, such as acetic acid. The dihydroxy stearic acid ester starting material may be prepared by treatment of oleic acid or ethyl oleate with hydrogen peroxide in acetic or formic acid in the presence of sulphuric acid as a catalyst to give p 9,10-dihydroxystearic acid which is then esterified. The azelaic acid semiester prepared as above may be treated with thionyl chloride to give the acid chloride, and the latter on reaction with a tertiary amine is converted to a dimer which on saponification with alcoholic potash and subsequent acidification gives civetone dicarboxylic acid. Alternatively, the dimer is boiled with aqueous alcohol to give the ethyl ester of civetone dicarboxylic acid which is useful for the preparation of civetone and dihydrocivetone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1141758A GB830637A (en) | 1958-04-10 | 1958-04-10 | A process for the preparation of azelaic acid semi-ester suitable for making civetone dicarboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1141758A GB830637A (en) | 1958-04-10 | 1958-04-10 | A process for the preparation of azelaic acid semi-ester suitable for making civetone dicarboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB830637A true GB830637A (en) | 1960-03-16 |
Family
ID=9985830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1141758A Expired GB830637A (en) | 1958-04-10 | 1958-04-10 | A process for the preparation of azelaic acid semi-ester suitable for making civetone dicarboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB830637A (en) |
-
1958
- 1958-04-10 GB GB1141758A patent/GB830637A/en not_active Expired
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