Action of peracetic acid on (+)-sabinol

Abstract

The compound said to have the constitution C₁₀H₁₈O₃, obtained by Henderson and Robertson from the action of peracetic acid on (+)-sabinol, has been shown to be p-menthane-1α,2β,4β-triol (C₁₀H₂₀O₃) by its synthesis from (+)-terpinen-4-ol. The origin of the triol from the sabinol reaction is discussed and it is suggested that it actually arises from terpinen-4-ol, present either as impurity or as a product of the reaction of acetic acid on sabinol. The products of this reaction have been investigated and terpinen-4-ol has been found to be present. (+)-2-endo-Hydroxy-1,4-cineole was obtained by acid-catalysed rearrangement of (+)-terpinen-4-ol α-epoxide.