油化学
Online ISSN : 1884-2003
ISSN-L : 0513-398X
D-12-オキシステアリン酸のワルデン反転
立花 太郎神原 英子
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ジャーナル フリー

1966 年 15 巻 2 号 p. 73-74

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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.
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