Benzaldehyde → Styrene Oxide

Participants

Reaction Steps

To a solution of diethyl zinc (1.8 ml of 1.1M solution in toluene, 2.0 mmol) in 1,2-dichloroethane (6 ml) was added chloroiododomethane (218 μl. 3 mmol) at -15° C. and the reaction mixture was stirred for 15 minutes. Tetrahydrothiophene (240 μl , 3 mmol) and benzaldehyde (1 mmol) were added and the reaction mixture was warmed to room temperature. After stirring at that temperature for 1 hour the reaction mixture was refluxed for one hour. After cooling to room temperature, the reaction mixture was diluted with dichloromethane (20 ml) and washed with saturated solution of NH4Cl (3×5 ml). The organic layer was dried over MgSO4. After filtration of the drying agent the solvent was removed in vacuo and the residue was chromatographed over silica (eluant petrol:dichloromethane (40:60) to give the title compound as a clear oil (92%).

Provenance & Evidence