PRODUCTION OF LONG-CHAIN BETA-HYDROXYCARBOXYLIC ACID OF HIGH OPTICAL PURITY

摘要

PROBLEM TO BE SOLVED: To industrially and advantageously produce the subject compound by reacting an optically active long-chain epoxyalkane with an alkali metal cyanide under specific conditions and then hydrolyzing the resultant compound with an alkali metal hydroxide under heating. SOLUTION: An optically active long-chain 1,2-epoxyalkane represented by formula I (R is an 8-20C long-chain alkyl; * is an asymmetric carbon atom) is reacted with an alkali metal cyanide (preferably potassium cyanide or sodium cyanide) in an aqueous solution of a lower alcohol (preferably methanol) at 60-90 (vol.) % concentration while regulating the pH of the reactional mixture to 10-14 to produce an optically active long-chain β-hydroxynitrile represented by formula II. The resultant compound represented by formula II is then hydrolyzed in the presence of aqueous hydrogen peroxide with an alkali metal hydroxide under heating to afford an optically active long-chain β-hydroxycarboxylic acid represented by formula III. Thereby, the objective compound can be synthesized in a short process under mild reactional conditions without using a special apparatus.