2-Phenylethanol → 2-Phenylethyl Acetate

In a dry 50-mL, two-necked, round-bottomed flask, vanadyl sulfate (8.2 mg, 0.05 mmol) in 3 mL of anhydrous CH3CN was placed. To the above mixture, 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 CH3CN (2 mL) was slowly added to the above bluish solution with residual suspended vanadyl sulfate, and the reaction mixture was stirred for 24 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 150.9 mg of 2-phenethyl acetate (92%) as colorless oil. The substrate, reaction time, and yield of this test are summarized in Entry 3 of the following Table 1.

1. customAfter completion of the reaction
2. customthe reaction mixture was quenched with cold, saturated aqueous NaHCO3 solution (5 mL)
3. customThe resulting separated organic layer
4. washwas washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. customThe crude product was purified by column chromatography on silica gel

ORD record

ord-b9e89751e1654c6680a3a3ad875332cd

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06541659B1