Hydrochloric Acid → HCID 54110740, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl-8-benzyloxy-3,7-dimethyl-2-octenoate (94.6 g, 0.31 M) in ether (1.4 l) is added to a slurry of lithium aluminum hydride (47.3 g, 1.25 M) in ether (3.3 l) at 0° C. and the reaction mixture is allowed to stir at 0° C. for 4 hours. Wet ether (750 ml) is added slowly and the mixture is acidified with 1N hydrochloric acid. The organic phase is separated, the aqueous phase is extracted with ether and the combined organic extracts are washed with brine and dried (Na2SO4). The solvent is removed in vacuo to give the crude product (77.6 g, 95%). Purification over silica gel using an ethyl acetate/hexane gradient as the eluent gives fractions of varying mixtures of isomers. A collection of fractions that gives 17.7 g of 8-benzyloxy-3,7-dimethyl-2-octenolwith an 85/15 E/Z isomer ratio by gas chromatography analysis is used in the next step:

Provenance & Evidence