Ethyl phenylacetate → 2-Phenylethanol

Participants

Reaction Conditions

Reaction Steps

To a dry Schlenk tube under argon was added 50 mg of titanocene dichloride (0.2 mmol) and 2 mL of tetrahydrofuran. The slurry was cooled to -78° C. in a dry ice/acetone bath and 250 μL of a 1.6M hexane solution of n-butyl lithium. (0.4 mmol) was added. After stirring for 15 minutes, 1.8 mL of triethoxysilane (10 mmol was added, followed by 500 μL ethyl 2-phenylethanoate (3.0 mmol), and the reaction mixture was allowed to warm to room temperature. The reaction mixture bubbled vigorously. When the bubbles subsided, the reaction mixture began to warm rapidly, causing tetrahydrofuran to begin refluxing. When the mixture cooled back to room temperature, the catalyst was quenched by exposure to air until the color changed from dark brown to yellow. Next, 5 mL of tetrahydrofuran, 15 mL of EtOH, and 0.6 g of NaOH (15 mmol) were then added. After stirring for 2 hours, 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), the combined organic extracts were dried over MgSO4, filtered, and concentrated by rotary evaporation. The crude product was purified by flash Chromatography (ether:hexane=1:1), which afforded 300 mg (82% yield) of phenethyl alcohol.

Provenance & Evidence