Benzaldehyde → Styrene Oxide

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.

1. stirringthe mixture was stirred for 25 minutes
2. customto rise to 19° C
3. stirringthe reaction mixture was stirred until it
4. customreached room temperature
5. stirringThe reaction mixture was stirred at room temperature for 1 hour after which it
6. washwashed with a saturated solution of NH4Cl (3×5 ml)
7. dry with materialThe organic layer was dried over MgSO4

ORD record

ord-1732280c406e4e31962ae699fb5225da

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05703246