Ethanol → Ethyl phenylacetate

A solution of phenylacetic acid (50 g, 0.36 mol) in ethanol (150 mL) is treated with catalytic amount of sulfuric acid (4 mL). The reaction mixture is refluxed for 4 h. The reaction is then concentrated in vacuo. The residue is dissolved in diethyl ether (300 mL) and washed with saturated aqueous sodium bicarbonate solution (2×50 mL) and water (1×100 mL). The organic layer dried over sodium sulfate filtered and concentrated in vacuo to give phenylacetic acid ethyl ester as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.2 (t, J=7.2, 3H), 3.6 (s, 2H), 4.1 (q, J=7.2, 2H), 7.3 (m, 5H); MS 165 [M+1]+.

1. temperatureThe reaction mixture is refluxed for 4 h
2. concentrationThe reaction is then concentrated in vacuo
3. dissolutionThe residue is dissolved in diethyl ether (300 mL)
4. washwashed with saturated aqueous sodium bicarbonate solution (2×50 mL) and water (1×100 mL)
5. dry with materialThe organic layer dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-79062ff4919d482e991bd8d96c996c04

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07750020B2