• 약학회지
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• 제35권4호
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• pp.335-340
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• 1991

The synthetic product of 1-hydroxymethyl-p-mentha-8-ene-2-one was afforded by the reaction between dihydrocarvone and formaldehyde. This reaction involves the aldol condensation. The preferential position of formaldehyde is methyl substituted .alpha.-carbon atom where these enols are regiospecifically formed. The hydroxymethylation of dihydrocarvone was also proved to happen regiospecifically in the position of .alpha.-methyl substituted ketone. When 1-hydroxymethyl-p-mentha-8-ene-2-one reacted with LiAIH$_{4}$, 1-hydroxymethyl-p-mentha-8-ene-2$\beta$-ol obtained. 1-Hydroxymethyl-p-mentha-8-ene-2-one reacted with PDC and chromic acid to give 1-formyl-p-mentha-8-ene-2-one and 1-carboxy-p-mentha-8-ene-2-one. When the hydroxymethyl group of 1-hydroxymethyl-p-menta-8-ene-2-one was reducted to methyl group, 1-methyl-p-menta-8-ene-2-one was obtained. Some of these new compound have certain odor. I, II have woody aroma and IV, V have camphory odors. IX has flowery minty odor.