Preparing carboxylic acids from glycidonitriles
US3987094A · kind A · utility
Assignee
Inventor
Key dates
| Filing date | Dec 10, 1974 |
| Grant date | Oct 19, 1976 |
| Priority date | — |
| Expiry date | Dec 10, 1994 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C51/08
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Process for preparing carboxylic acids by (1) reacting a glycidonitrile with a carboxylic acid halide in the presence of a catalytic amount of a tertiary amine or acid salt thereof to form a 2-acyloxy-3-halo-propionitrile, (2) dehydrohalogenating the halogenated acylate from step (1) to form the acyloxy acrylonitrile intermediate (enol-acylate) (3) hydrolyzing the enol-acylate from step (2) with aqueous base to form the carboxylic acid salt, and (4) acidifying the carboxylic acid salt with acid to form the carboxylic acid. Salts of persulfate and hypochlorite ions can be added to destroy cyanide ion. The process can be used to prepare a wide variety of carboxylic acids, e.g., 2-(4'-isobutylphenyl)propionic acid, now known generally as ibuprofen, a highly active anti-inflammatory drug.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.