Ammonium Chloride → 3-(trans-4-(trans-4-Propylcyclohexyl)cyclohexyl)propanol

Participants

Reaction Steps

A solution of 3-(4′-Propyl-bicyclohexyl-4-yl)-propionic acid ethyl ester (22.0 g, 70 mmol) in THF (150 ml) is added dropwise to a suspension of lithium-aluminiumhydride (3.25 g, 86 mmol) in THF (250 ml) at reflux temperature. The reaction is heated under reflux for 1 h, cooled and poured onto sat. ammonium chloride solution. The mixture is acidified, extracted with ether and the combined organic layers are washed with brine and dried over sodium sulfate. The solvent is evaporated and the crude product is crystallised from isopropanol to give 3-(4′-propyl-bicyclohexyl-4-yl)-propan-1-ol as colourless crystals.

Provenance & Evidence