Preparing carboxylic acids from glycidonitriles

Details Preparing carboxylic acids from glycidonitriles Preparing carboxylic acids from glycidonitriles

1974-12-10

1976-10-19

Weinberger, Lorraine A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260239BA, 260287R, 26029388, 260295R, 2603264, 26032611R, 26032613R, 2603322A, 2603971, 260413, 260465D, 2604654, 260479R, 260488R, 260514R, 260514H, 260514G, 260514L, 260515P, 260518R, 260520R, 260521R, 260526N, 260534R, 260540, C07C 5102, C07C 5100

Patent

active

039870944

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.

REFERENCES:
patent: 2266771 (1941-12-01), Lange et al.
patent: 2764608 (1956-09-01), Blair
Deakin et al., J. Chem. Soc., 97, (1910), pp. 1968-1978.
Nowak, J. Org. Chem., 28, (1963), pp. 1182-1187.
Morrison et al., Organic Chemistry, 2nd Ed., (1966), pp. 582-583.
Malinouskii, Epoxides and Their Derivatives, (1965), pp. 188-192.

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