Acetophenone → 1-Phenylethanol

Participants

Reaction Conditions

Reaction Steps

A dry Schlenk tube under argon was charged with triethoxysilane (1.1 ml, 6.0 mmol) and acetophenone (580 μL, 5 mmol) and heated to 48° C. Titanium (IV), isopropoxide (75 μL, 0.25 mmol) was then added. After stirring at 48° C. for an hour the color changed to deep blue. After 6 hours the reaction mixture was cooled to room temperature. After 12 hours it was added to THF (5 mL). Aqueous NaOH (1 N, 15 mL) was then added to the solution. After vigorous stirring at room temperature for 1 hour, the reaction mixture was added to a water/ether mixture (100 mL each), shaken vigorously, and the organic layer was separated. The aqueous layer was washed with an additional 100 mL of ether, and the combined ether extracts were dried over MgSO4. Concentration in vacuo afforded 587 mg (97% yield, greater than 95% pure by NMR and GC) of sec-phenethyl alcohol as a slightly yellowish oil.

Provenance & Evidence