Reactions directed towards the synthesis of 5-(β-hydroxyethyl)-2-isopropylcyclohexanone

Abstract

Reduction of perillaldehyde by lithium in ammonia gives products the structures of which depend on reaction conditions. Shisool (p-menth-8- en-7-ol) undergoes double-bond migration in the presence of acids. The corresponding aldehyde, with dimethylsulfonium methylide, forms an oxiran which is comparatively unreactive, double-bond rearrangement or reduction accompanying the opening of the oxiran. The conversion of shisool into 5-(β-hydroxyethyl)-2-isopropylcyclohexanone was frustrated by only partial migration of the double bond.