Preparing carboxylic acids from glycidonitriles through enol acy

Details Preparing carboxylic acids from glycidonitriles through enol acy Preparing carboxylic acids from glycidonitriles through enol acy

1974-12-10

1976-08-17

Thomas, Jr., James O.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260514R, 260515A, 260540, 260520R, C07C 6352

Patent

active

039754316

ABSTRACT:
Process for preparing carboxylic acids by converting a glycidonitrile to the enol acylate via hydrohalogenation, acylation and dehydrohalogenation procedures, and conversion of the enol acylate to the carboxylate salt with a base and of the salt to the carboxylic acid with acid. Cyanide content in the mixture is destroyed by adding persulfate or hypochlorite salts. This process, can be used, e.g., to prepare 2-(4'-isobutylphenyl)propionic acid, now known generically as ibuprofen, a highly active anti-inflammatory drug, as well as a host of other useful carboxylic acids.

REFERENCES:
stork et al., J.A.C.S., 82, pp. 4315-4323 (1960).
Wagner et al., Synthetic Organic Chem., John Wiley & Sons, Inc., New York, N. Y., pp. 35-39, 169-170, & 481-483 (1965).
Contacuzene et al., "Tetrahedron Letters," pp. 2237-2242 (1966).

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