YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Studies on Lipoic Acid. III
Synthesis of Alkyl 8-Alkoxy- and 8-Acyloxy-6-oxoöctanoate. (2)
Shojiro YurugiTomiyoshi FushimiMitsuo Numata
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1960 Volume 80 Issue 10 Pages 1317-1321

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Abstract
Heating of alkyl 8-chloro-6-oxoöctanoate (III, IV) with fatty acid results in formation of alkyl 6-oxo-7-octenoate (V, VI) and alkyl 8-acyloxy-6-oxoöctanoate (VII, VIII). Addition of a dehydrochlorination agent in this reaction was found to shorten the reaction time and increase the yield of the product. In the reaction of alkyl 8-chloro-6-oxoöctanoate (III, IV) and alcohols, ester exchange occurs due to the liberated hydrogen chloride and alkyl 8-alkoxy-6-oxoöctanoate (IX, X) is formed. Methyl 8-acetoxy-6-oxoöctanoate (VII:R′=CH3) and methyl 8-methoxy-6-oxoöctanoate (IX:R=CH3) undergo mutual transition in the presence of a suitable catalyst.
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