Synthesis of furyl analogues of acyclic monoterpenes

Abstract

Starting from furfural and 5-methyfurfural, the furyl analogues of linalool, geraniol, citral, citronellol and citronellal, in which the isobutenyl moiety was replaced by a furyl substituent, have been synthesized. The olfactory properties of the new compounds prepared are of the corresponding parent terpene type; however, a positive influence of the methyl group in the furan ring on the odour was observed. The relative vapour pressures of furyl analogue alcohols were determined by SPME-GC and shown to be lower by a factor of 1.6-2.9 as compared to their corresponding par- ent terpene alcohols. Copyright © 2005 John Wiley & Sons, Ltd.