2-Phenylethanol → 2-Phenylethyl Acetate

In a dry 50-mL, two-necked, round-bottomed flask, vanadyl chloride (1.9 mg, 0.01 mmol) in 3 mL of anhydrous CH2Cl2 was placed. To the above solution, acetic anhydride (153.1 mg, 141.5 μL, 1.5 mmol) was slowly added at ambient temperature. After about 10 min, a solution of 2-phenylethanol (122 mg, 119.3 μL, 1.0 mmol) in CH2Cl2 (2 mL) was slowly added to the above brownish solution, and the reaction mixture was stirred for 7.5 hours. After completion of the reaction as monitored by TLC, the reaction mixture was quenched with cold, saturated aqueous NaHCO3 solution (5 mL). The resulting separated organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. The crude product was purified by column chromatography on silica gel to yield 154.2 mg of 2-phenethyl acetate (94%) as colorless oil. The substrate, reaction time, and yield of this test are summarized in Entry 2 of the following Table 1.