Ethanol → Ethyl 5-chloro-2-methylbenzoate

Temperature

0 °C

A mixture of 5-chloro-2-methylbenzoic acid (3.00 g, 17.5 mmol) in ethanol (30 mL) was cooled to 0° C. with an ice bath and thionyl chloride (12.5 mL, 105.5 mmol) was added dropwise, over 30 minutes. After this time, the mixture was warmed to room temperature for 1 h, then transferred to an oil bath, and heated to 70° C. overnight. The mixture was then cooled to room temperature and concentrated under reduced pressure. The solids obtained were then redissolved in diethyl ether (50 mL) and washed with 1 N sodium hydroxide (50 mL), brine (50 mL), dried over magnesium sulfate, and concentrated under reduced pressure to afford ethyl 5-chloro-2-methylbenzoate as a clear oil: 1H NMR (500 MHz, CDC13) δ 7.88 (d, J=2.5 Hz, 1H), 7.34 (dd, J=8.5, 2.5 Hz, 1H), 7.17 (d, J=8.5 Hz, 1H), 4.36 (q, J=7.5 Hz, 2H), 2.56 (s, 3H), 1.39 (t, J=7.5 Hz, 3H); ESI MS m/z 199 [M+H]+.

1. temperatureAfter this time, the mixture was warmed to room temperature for 1 h
2. customtransferred to an oil bath
3. temperatureheated to 70° C. overnight
4. temperatureThe mixture was then cooled to room temperature
5. concentrationconcentrated under reduced pressure
6. customThe solids obtained
7. washwashed with 1 N sodium hydroxide (50 mL), brine (50 mL)
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-f3f4033727014c169a472b82ebe52a1c

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110681B2