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

Temperature

25 °C

A solution of 4-(methanesulfonyl)phenyl acetic acid (43.63 g, 0.204 mol) in methanol (509 mL) was treated slowly with concentrated sulfuric acid (2 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 residue was diluted with ethyl acetate (800 mL). The organic phase was washed with a saturated aqueous sodium bicarbonate solution (1×200 mL) and a saturated aqueous sodium chloride solution (1×200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 1/1 hexanes/ethyl acetate) afforded 4-(methanesulfonyl)phenyl acetic acid methyl ester (45.42 g, 98%) as a yellow oil which solidified to a cream colored solid upon sitting over time at 25° C.: mp 78–80° C.; EI-HRMS m/e calcd for C10H12O4S (M+) 228.0456, found 228.0451.

1. customThe resulting reaction mixture
2. temperaturewas heated
3. temperatureunder reflux for 19 h
4. concentrationconcentrated in vacuo
5. customto remove methanol
6. additionThe residue was diluted with ethyl acetate (800 mL)
7. washThe organic phase was washed with a saturated aqueous sodium bicarbonate solution (1×200 mL)
8. dry with materiala saturated aqueous sodium chloride solution (1×200 mL), dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-7f718ed252864e63ae3be49d4b96fd15

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105671B2