Acetophenone → 1-Phenylethanol

Temperature

48 °C

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.

1. temperatureAfter 6 hours the reaction mixture was cooled to room temperature
2. stirringAfter vigorous stirring at room temperature for 1 hour
3. stirringshaken vigorously
4. customthe organic layer was separated
5. washThe aqueous layer was washed with an additional 100 mL of ether
6. dry with materialthe combined ether extracts were dried over MgSO4
7. concentrationConcentration in vacuo

ORD record

ord-4866a2b3bd82475caffea942203f16ee

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05220020