Sulfuric Acid → Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

2-Hydroxy-3-methylbenzoic acid (24.9 g, 0.164 mol) was dissolved in methanol (200 mL), then sulfuric acid (1.75 mL, 32.8 mmol) was added thereto, and then the reaction mixture was refluxed for 7 days. After the reaction mixture was poured into saturated aqueous NaHCO3 solution (300 mL), methanol was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (500 mL), then the organic layer was washed with saturated aqueous NaHCO3 solution (200 mL) and saturated brine (100 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure to give the titled reference compound (23.0 g) as a pale brown oil. (Yield 84%)

1. temperaturethe reaction mixture was refluxed for 7 days
2. customwas removed under reduced pressure
3. extractionThe aqueous layer was extracted with ethyl acetate (500 mL)
4. washthe organic layer was washed with saturated aqueous NaHCO3 solution (200 mL) and saturated brine (100 mL) successively
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was removed under reduced pressure

ORD record

ord-04e2c82f84c145c59254a66153511e5e

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420635B2