Dihydro-beta-ionone → Dihydro-beta-ionol

Participants

Reaction Steps

Dihydro-beta-ionone (J. Am. Chem. Soc., 108, 7314 (1986)) is reduced with sodium borohydride in ethanol in the usual fashion to provide 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanol as a colorless oil. This is coupled with 4-hydroxybenzaldehyde by the method of example 13, and the resulting aldehyde is chain-extended and condensed with glyoxylic acid by the methods of example 1. The title compound is obtained as a colorless solid, mp 99°-101° after recrystallization from hexane-chloroform

Provenance & Evidence