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

Temperature

25 °C

A solution of 4-(methylthio)phenylacetic acid (6.91 g, 37.9 mmol) in methanol (100 mL) was treated slowly with concentrated sulfuric acid (1 mL). The resulting reaction mixture was heated under reflux for 19 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The resulting residue was diluted with ethyl acetate (200 mL). The organic layer was washed with a saturated aqueous sodium bicarbonate solution (3×300 mL) and a saturated aqueous sodium chloride solution (1×100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford (4-methylsulfanyl-phenyl)-acetic acid methyl ester (7.28 g, 98%) 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 19 h
4. concentrationconcentrated in vacuo
5. customto remove methanol
6. additionThe resulting residue was diluted with ethyl acetate (200 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-66bb187cab124bc6a1b026c92a660f45

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441184B1