Acetophenone → 1-Phenylethanol

Participants

Reaction Conditions

Reaction Steps

To a dry Schlenk tube under argon was added 37.6 mg (0.15 mmol) of a titanocene dichloride and 3 mL of tetrahydrofuran. The slurry was cooled to -78° C. and a 1.64 M hexane solution of n-butyl lithium (190 μL, 0.3 mmol) was added. After stirring for 15 minutes, triethoxysilane (140 μL, 0.75 mmol) was added. The black mixture was allowed to warm to 0° C., then acetophenone (350 μL, 3.0 mmol), followed by more triethoxysilane (700 μL, 3.75 mmol) were added. The reaction mixture was allowed to stir for 6 hours at room temperature. The Schlenk tube was opened to air and 5 mL of water were added and allowed to stir at room temperature for 1 hour. A solution of 5 M NaOH (1 mL) was added and allowed to stir. When the reaction mixture had turned to a white slurry additional 5M NaOH and 5 mL of tetrahydrofuran were added. After stirring for 1 hour, the mixture was added to a water/ether mixture (150 mL each), shaken vigorously, and the layers were then separated. The aqueous layer was extracted with ether (2×50 mL) and the combined organic extracts were dried over MgSO4, filtered, and concentrated by rotary evaporation. The crude product was purified by flash chromatography (ether:hexane=1:2), which yielded 295 mg (80% yield) of sec-phenethyl alcohol.

Provenance & Evidence