The Synthesis of Carvone from α-Terpinyl Acetate

Abstract

Abstract (1) Oxidation of dl-α-terpineol with tert-butyl chromate yeilded 8-hydroxypiperitone, which has not previously been described, 8-hydroxycarvotanacetone and homoterpenyl methyl ketone. In this case the oxidative fission of the double bond in the ring took place to a remarkable extent. (2) Oxidation of dl-α-terpinyl acetate with tert-butyl chromate gave 8-acetoxypiperitone, 8-acetoxycarvotanacetone, (neither have previously been described) and homoterpenyl methyl ketone. In this oxidation the cleavage of the ethylenic linkage was suppressed, and the yield of 8-acetoxycarvotanacetone was relatively good. Moreover, the effects of the solvent, acetic acid, benzoyl peroxide, air and the reaction temperature, on the yield of 8-acetoxycarvotanacetone wre investigated. (3) 8-acetoxycarvotanacetone was converted into dl-carvone when acetic acid was eliminated by pyrolysis. (4) The synthesis of carvone from α-terpinyl acetate was attiained through the intermeidate of 8-acetoxycarvotanacetone The overall of carvone from α-terpinyl acetate was 28% mole%.