Preparation of carboxylic acids from glycidonitriles with ionic

Details Preparation of carboxylic acids from glycidonitriles with ionic Preparation of carboxylic acids from glycidonitriles with ionic

1976-04-23

1977-05-03

Weinberger, Lorraine A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260239BA, 260287R, 26029388, 260295R, 2603264, 26032611R, 26032613R, 2603322A, 2603452, 2603457, 2603971, 260413, 260465R, 2604651, 260479R, 260488R, 260514R, 260514H, 260514G, 260514L, 260515A, 260515P, 260520R, 260521R, 260526N, 260534R, 260535R, 260539R, 260540, C07C 5100

Patent

active

040214788

ABSTRACT:
Process for preparing carboxylic acids by converting a glycidonitrile to a 2-oxopropionitrile via use of an ionic Lewis acid, and conversion of the 2-oxopropionitrile to the carboxylate salt with a base and of the salt to the carboxylic acid with acid.
The process is especially useful for the preparation of 2-(p-isobutylphenyl)propionic acid, (lbuprofen), also known as Motrin, a known and highly active antiinflammatory agent as well as a host of other carboxylic acids which are known in the art as useful compounds.

REFERENCES:
gerkin, (Univ. of California Thesis, 1968), Available through Univ. Microfilms, Inc., Ann Arbor, Mich., Order No. 70-2065, pp. 15-20, 38-43, 54, 55, 94-96, 154, 155, 194, 195, 197, 203 & 204.
McDonold et al., J. Org. Chem., 35, pp. 2942-2947 (1970).
March, "Advanced Organic Chemistry: Reactions, Mechanisms and Structure," p. 288 (1968).
Thyagarajan, "Mechanisms of Molecular Migrations," vol. 3, pp. 91-96 (3-30-71).
Hine, "Physical Organic Chemistry," 2nd Ed., p. 161.
Petty, J. Am. Chem. Soc., 76, pp. 4385-4389, (9-5-74).

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