Methanol → Methyl 2-(4-(methylthio)phenyl)acetate

Temperature

25 °C

A solution of 4-(methylthio)phenylacetic acid (21.21 g, 116.38 mmol) in methanol (291 mL) was treated slowly with concentrated sulfuric acid (3 mL). The resulting reaction mixture was heated under reflux for 3 d. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The resulting residue was diluted with diethyl ether (600 mL). The organic layer was washed with a saturated aqueous sodium bicarbonate solution (3×300 mL) and a saturated aqueous sodium chloride solution (1×300 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford (4-methylsulfanyl-phenyl)-acetic acid methyl ester (20.95 g, 92%) as a yellow liquid which was used without further purification: EI-HRMS m/e calcd for C10H12O2S (M+) 196.0558, found 196.0559.

1. customThe resulting reaction mixture
2. temperaturewas heated
3. temperatureunder reflux for 3 d
4. concentrationconcentrated in vacuo
5. customto remove methanol
6. additionThe resulting residue was diluted with diethyl ether (600 mL)
7. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution (3×300 mL)
8. dry with materialThe organic layer was dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-b118fea4c919434fb4abab1240c3a749

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06320050B1