Methanol → HCID 12067651, compound

Temperature

25 °C

A solution of (3-chloro-4-methylsulfanyl-phenyl)-acetic acid (8.00 g, 36.92 mmol) in methanol (200 mL) was treated slowly with concentrated sulfuric acid (1 mL). The resulting reaction mixture was heated under reflux overnight. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to remove methanol. The resulting residue was dissolved with ethyl acetate (50 mL). The organic layer was washed with water (1×50 mL). The water layer was further extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with a saturated aqueous sodium bicarbonate solution (1×25 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo to afford (3-chloro-4-methylsulfanyl-phenyl)-acetic acid methyl ester (7.28 g, 85.5%) as a yellow oil which was used without further purification: EI-HRMS m/e calcd for C10H11ClO2S (M+) 230.0168, found 230.0166.

1. customThe resulting reaction mixture
2. temperaturewas heated
3. temperatureunder reflux overnight
4. concentrationconcentrated in vacuo
5. customto remove methanol
6. dissolutionThe resulting residue was dissolved with ethyl acetate (50 mL)
7. washThe organic layer was washed with water (1×50 mL)
8. extractionThe water layer was further extracted with ethyl acetate (3×20 mL)
9. washThe combined organic layers were washed with a saturated aqueous sodium bicarbonate solution (1×25 mL)
10. dry with materialThe organic layer was then dried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORD record

ord-184f13ca676542a2b4bc21a8fc5ed096

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06545155B2