Methanol → Methyl 2-chloro-3-methylbenzoate

Temperature

80 °C

A mixture of 2-chloro-3-methylbenzoic acid (25.0 g, 146 mmol), conc. sulfuric acid (2 mL) and methanol (160 mL) was stirred at 80° C. for 3 hr. The reaction mixture was concentrated, was diluted with ethyl acetate and neutralized with 8N aqueous sodium hydroxide solution. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered through a basic silica gel pad. The filtrate was concentrated under reduced pressure to give the title compound (18.0 g, 66%) as a pale-orange oil. The obtained compound was used for the next reaction without further purification.

1. concentrationThe reaction mixture was concentrated
2. additionwas diluted with ethyl acetate and neutralized with 8N aqueous sodium hydroxide solution
3. customThe organic layer was separated
4. washwashed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered through a basic silica gel pad
7. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-5b1c6dec7af7495a9e6293bc65531a2d

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2