Hydration of Caryophyllene with Chloroacetic Acids

Abstract

Hydration of caryophyllene [ 1 ] with an equimolar amount of mono-, di-and trichloroacetic acids has been studied under anhydrous and/or aqueous conditions. Four alcohols were obtained from the products (yield 7S% at best) and their structures were assigned to be β-caryophyllene alcohol (caryolan-1-ol) [1 b], dihydroneocloven-4 β-ol [1 c], dihydrocaryophylIen-4-ol [1 d], and dihydrocloven-9#-ol [1 a] on the basis of their physical constants, IR, NMR and MS spectra. Usually [1 a] was a major product, amounting to 72% of the hydration product under the best conditions. The compounds [1 b], [1 c] and [1 d] are new sesquiterpene alcohols. © 1976, The Chemical Society of Japan. All rights reserved.