Synthesis of 2-(2-Hydroxy-4-Methylphenyl)-Prop-1-Enyl Acetate via Thermal Rearrangement of 2-Methyl-2-(2-Hydroxy-4-Methylphenyl)-Oxirane

Abstract

Recently Bohlmann, Niedballa and Schulz 2 isolated from the roots of Gaillardia aristata the oxirane 1, the enol ester 2 and a number of other compounds related to thymol. Hence, it was considered of interest to synthesise the oxirane 3. It was anticipated that since in one of the conformers of 3, the oxirane ring is in spatial juxtaposition with the acetate group, acyl migration may be induced via treatment with acids or other methods, to transform 3 to the enol ester 4.