Ethyl cyclohexylideneacetate → 2-Cyclohexylideneethanol

To a stirred solution of ethyl cyclohexylideneacetate (see route to this by Wadsworth and Emmons in Org. Synth. Coll. Vol 5 547) (3.00 g, 17.8 mmol) in dry ether (50 ml) under an atmosphere of nitrogen at 0° C. was added lithium aluminium hydride (407 mg, 10.7 mol) portionwise and the mixture stirred for 2 hours before quenching with dilute hydrochloric acid (2M; 20 ml). The mixture was filtered and the aqueous layer was separated and extracted further with ether (2×25 ml) and the combined ether layers washed with water (2×25 ml) and saturated sodium chloride solution (25 ml) and then dried over MgSO4. Filtration and evaporation of the solvent and distillation of the residue gave 2-cyclohexylidene ethanol (2.16 g, bp. 112° C. at 10 mmHg [Kugelrohr]).