Benzaldehyde → Styrene Oxide

Participants

Reaction Steps

To a solution of diethyl zinc (18 ml of 1.1M solution in toluene, 20 mmol) in 1,2-dichloroethane (60 ml) was added chloroiododomethane (2.18 ml, 30 mmol) at -15° C. and the reaction mixture was stirred for 15 minutes. Tetrahydrothiophene (2.40 ml, 30 mmol) was added at -15° C. and the mixture was stirred for 25 minutes. During this time the temperature was allowed to rise to 19° C. Benzaldehyde (2.12 ml, 20 mmol) was added and the reaction mixture was stirred until it reached room temperature. The reaction mixture was stirred at room temperature for 1 hour after which it was diluted with dichloromethane (20 ml) and washed with a saturated solution of NH4Cl (3×5 ml). The organic layer was dried over MgSO4. The resulting solution was analysed by gas chromatography and the title compound was found to be present.

Provenance & Evidence