Ethanol → Ethyl 2-(2-chlorophenyl)acetate

A mixture of 2-(2-chlorophenyl)acetic acid (10 g, 58.6 mmol) in EtOH (Volume: 152 ml) was treated with H2SO4 (1.719 ml, 32.2 mmol). The result mixture was refluxed overnight. The heat was removed, and the reaction mixture was concentrated. The resulting oil was dissolved in EtOAc and CAREFULLY treated with aqueous Na2CO3 (3.47 g, 32.8 mmol) (CAUTION: Gas evolution) until the solution remained basic and no further gas evolution was seen. The EtOAc layer was then removed and the aqueous layer was again extracted two times with EtOAc. The combined organic layers were then washed with brine, dried over Na2SO4 and concentrated in vacuo to obtain ethyl 2-(2-chlorophenyl)acetate (11.32 g, 57.0 mmol, 97% yield). LC-MS (M+H)+=199.1. 1H NMR (500 MHz, CD3OD) δ 7.41 (ddd, J=16.8, 5.6, 3.5 Hz, 1H), 7.35 (dd, J=5.5, 3.7 Hz, 1H), 7.28 (dd, J=5.8, 3.7 Hz, 2H), 4.17 (q, J=7.0 Hz, 2H), 3.80 (s, 2H), 1.26 (t, J=7.2 Hz, 3H).

1. temperatureThe result mixture was refluxed overnight
2. customThe heat was removed
3. concentrationthe reaction mixture was concentrated
4. dissolutionThe resulting oil was dissolved in EtOAc
5. customThe EtOAc layer was then removed
6. extractionthe aqueous layer was again extracted two times with EtOAc
7. washThe combined organic layers were then washed with brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated in vacuo

ORD record

ord-d8307e2257b643d0ab243b0ea5f74f3c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710061B2