Preparation of 2-hexyl-4-Acetoxytetrahydrofuran

Abstract

2-Hexyl-4-acetoxytetrahydrofuran is a flavor compound with a sweet, floral-fruity odour. Two different methods for its preparation were investigated starting from 1-decen-4-ol. 1-Decen-4-ol was transformed to 2-hexyl-4-acetoxytetrahydrofuran through mesylation, dihydroxylation, intramolecular nucleophilic substitution and acetylation in overall 70% yield; alternatively, 1-decen-4-ol was epoxidised to 1,2-epoxy-4-decanol, followed by acetylation and dehydration to produce the desired product in overall 48% yield. The two methods gave the product with poor and opposite diastereoselectivity but both routes have advantages on yield or ease of operation over the literature procedure.