Methanol → Benzoic acid, 2,3-dichloro-, methyl ester

A solution of 2,3-dichlorobenzoic acid (100 g, 0.526 mol) in methanol (1 L), was added H2SO4 (20 mL). The solution was stirred under reflux overnight. The reaction mixture was cooled and concentrated. The resulting residue was diluted with water (100 mL) and ethyl acetate (1 L). Then the organic layer was washed with aq. NaHCO3 and brine, dried over Na2SO4, filtered and the filtrate was concentrated to provide the titled compound (99 g, 92%), as a white solid; 1H NMR (300 MHz, CDCl3) δ ppm 3.95 (s, 3H), 7.27 (t, J=7.8 Hz, 1H), 7.60 (dd, J=1.8, 7.8 Hz, 1H), 7.66 (dd, J=1.8, 7.8 Hz, 1H).

1. temperatureunder reflux overnight
2. temperatureThe reaction mixture was cooled
3. concentrationconcentrated
4. additionThe resulting residue was diluted with water (100 mL) and ethyl acetate (1 L)
5. washThen the organic layer was washed with aq. NaHCO3 and brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationthe filtrate was concentrated

ORD record

ord-45d3bc2f4a1144cf941441c4d4bdeaa1

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096605B2