Reaction of 2,3-epoxypinane with methanol in presence of sodium methoxide

Abstract

1. Under the action of sodium methoxide in methanol 2,3-epoxypinane forms trans-2(10)-pinen-3-ol (mixture of l- and d l-forms) and 3-pinanone (mixture of d- and d l-forms). 2. Under the conditions of the reaction of 2,3-epoxypinane with methanol 3-pinanone may be formed in two ways: 1) mainly directly by the isomerization of the epoxide into the ketone, and 2) by the isomerization of the primary reaction product 2(10)-pinen-3-ol under the action of the base. © 1968 Consultants Bureau.