Synthesis of furyl analogues of acyclic monoterpenes

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 parent terpene alcohols. Copyright © 2005 John Wiley & Sons, Ltd.