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

4-Methylsalicylic 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-methylsalicylate.

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-Eintrag

ord-a1b5ce696ab84fdca4aaa23787305d0b

Quelldatensatz

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05859210