Sodium Hydroxide → Styrene Oxide

Participants

Reaction Steps

A solution of (+)-2-chloro-1-phenylethanol (156.6 mg, 1.0 mmol, 97.5% ee) in dichloromethane (2.0 ml) and a 2.0 M aqueous solution of sodium hydroxide (1.0 ml, 2.0 mmol) were mixed and stirred at room temperature for 4 hours. To the solution was added dichloromethane (2.0 ml), and the dichloromethane layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was removed by evaporation. The residue was purified by silica gel column chromatography to give a desired compound, (+)-styrene oxide (115.2 mg; yield: 95.9%; optical purity: 97.5% ee).

Provenance & Evidence