Introduce 84 ml (0.3 mole) Vitride reducing agent (e.g. sodium-bis-(2-methoxy-ethoxy)aluminum hydride) and about 250 ml of dry benzene (or toluene) into 3-neck flask fitted with a condenser and air-stirrer and bring to reflux. Add dropwise in a course of 30 minutes a solution of 30 g trans-4(4-heptylcyclohexyl)benzoic acid in benzene and continue to reflux for additional 3-4 hours. Mixture is then cooled to room temperature and introduced slowly with stirring into a 20% aqueous HCl solution plus ice. After addition, the mixture is vigorously stirred for another 20 to 30 minutes and resulting layers are then separated. Evaporation of benzene yielded the desired compound, trans-4-(4-heptylcyclohexyl)benzylalcohol in typically 99.9% purity by gas chromatography and yields over 95%.
