Improved method of preparation of α‐substituted fatty acids

Abstract

AbstractThe previously published methods for the syntheses of α‐substituted fatty acids, as developed by Pfeffer et al. and Konen et al., were improved by using the dimethylamides instead of the free carboxylic acids and changing the solvent system to eliminate hexamethylphosphoramide, a known carcinogen. The improved method cuts the use of metalating agent in half, drastically reduces refrigeration requirements, and permits the preparation of larger batches. A Grignard reagent can be used in place ofn‐butyllithium as metalating agent but gives substantially poorer yields. The syntheses of α‐hydroxylauric acid and α‐butyllauric acid are described.