Methanol → Methyl 2-chloro-3-methylbenzoate

Temperature

80 °C

A mixture of 2-chloro-3-methylbenzoic acid (25.0 g, 0.146 mol), conc. sulfuric acid (2 mL) and methanol (160 mL) was stirred 80° C. for 3 hr. The reaction mixture was concentrated, and the residue 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 pad filled with basic silica gel. The solvent 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 operation.

1. concentrationThe reaction mixture was concentrated
2. additionthe residue was diluted with ethyl acetate
3. customThe organic layer was separated
4. washwashed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered through a pad
7. additionfilled with basic silica gel
8. concentrationThe solvent was concentrated under reduced pressure

ORD record

ord-d11826f634c54653b5b94e3f3c74d2a8

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2