Abstract
An atempt was made to prepare L-12-hydroxystearic acid (L-acid) from commercial D-12-hydroxystearic acid (D-acid) by the Walden inversion. D-Acid was converted to the methyl ester, and then to the tosylate by reaction with p -toluenesulfonyl chloride. The Walden inversion occured when the tosyl group was acetylated with sodium acetate in acetic acid containing acetic anhydrous. L-Acid was obtained by saponifying the acetate with potassium hydroxide. The yield of the crude product was about 61%, based on the D-acid. The metal soaps of D-acid and L-acid formed helical aggregates from mineral oil, exhibiting the enantiomorphic relationship for the direction of the twist.
