Studies on the Reduction of Terpenes with Sodium in Aqueous-ammonia

Part III. On the Reduction (-)-Carvone

Abstract

On the reduction of (-)-carvone with sodium in aqueous-ammonia, the predominant product was found to be (-)-dihydrocarveol, a new stereoisomer. From this fact, it might be concluded that this reduction method is stereospecific for (-)-carvone, similary as in the case of (-)-menthone. By the catalytic hydrogenation of (-)-dihydrocarveol, a new stereoisomer of carvomenthol has also been prepared. It is noteworthy that (-)-dihydrocarveol has the same conformation (e, e, e) as that of (-)-menthol, which was also quantitatively obtained from (-)-menthone by application of our method of reduction reported previously.