Przemysl Chemiczny, Vol.89, No.4, 577-581, 2010
Synthesis and odor characteristics of esters of dimethylsubstituted cyclohexenols
Three geminal Me2-substituted racemic cyclohex-2-en-1-ols (I) were synthesized by conversion of resp. dimethylcyclohex-1,3-dions with EtOH in presence of TsOH and following redn. with LiAlH(4), enriched in particular R and S-enantiomers by enzymatic esterification and following hydrolysis, esterified with AcCl or EtCOCl to I acetates or propionates, resp., and then tested for odors. The I esters with geminal Me groups in alpha-position to the double bond and in gamma-position the ester groups showed the best odoriferous properties. Odors of most I ester S-enantiomers were more pleasant than the analog R-enantiomers but less intensive.