DL-Mentholの合成

概要

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Piperitenone [I] with a relatively high purity is obtained by the reaction of methyl vinyl ketone with an excess of mesityl oxide in the presence of potassium hydroxide. A mixture of menthone [II] and isomenthone [II'] is formed by a routine catalytic reduction of I over palladium-carbon but isomerization of I to thymol is very slight. The reaction product from a mixture of II and II' in various ratios and hydroxylamine in alkaline medium is mostly menthone oxime [III], and isomenthone oxime [III'] is hardly formed. On the contrary, a mixture of III and III' is obtained by the same reaction in neutral or acidic medium. III is converted into menthylamine [IV] by its reduction with metallic sodium in ethanol. Pure DL-menthol [V] is synthesized by a routine diazotation of IV, where the amino group in the molecule of IV is converted into hydroxyl group without inversion.
公益社団法人日本薬学会の論文
1968-04-25