Methanol → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

4-Methyl-2-hydroxybenzoic acid (100 g, 658 mmoles) was dissolved in anhydrous methanol (500 mL) and concentrated sulfuric acid (25 mL) was added carefully. The solution was refluxed for 18 hours, then cooled to room temperature. The reaction mixture was concentrated to about 150 mL, and ethyl acetate (250 mL) was added. The ethyl acetate solution was washed twice with saturated aqueous sodium bicarbonate (250 mL portions) and then with saturated aqueous sodium chloride (100 mL). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered, and evaporated to a clear, reddish-brown liquid. This crude product was vacuum distilled (oil pump) to afford a clear, viscous liquid that solidified on standing to afford 98.1 g (90% yield) of methyl 4-methyl-2-hydroxybenzoate.

1. temperatureThe solution was refluxed for 18 hours
2. concentrationThe reaction mixture was concentrated to about 150 mL, and ethyl acetate (250 mL)
3. additionwas added
4. washThe ethyl acetate solution was washed twice with saturated aqueous sodium bicarbonate (250 mL portions)
5. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated to a clear, reddish-brown liquid
8. distillationdistilled (oil pump)
9. customto afford a clear, viscous liquid that solidified

ORD record

ord-5b2c3b52787a4838a0ae305b8c3d0c99

Source dataset

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06156884