Potassium Hydroxide → Methyl 2-(3-mercaptophenyl)acetate

A mixture of (3-dimethylcarbamoylsulfanyl-phenyl)-acetic acid methyl ester (2.0 g, 7.9 mmol), potassium hydroxide (1.4 g, 24 mmol) methanol (50 mL), and water (5 mL) is stirred at reflux 3 hr. The mixture is concentrated, and product partitioned between 1M aqueous hydrochloric acid (50 mL) and ethyl acetate (3×75 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is taken up in methanol (50 mL), 2 mL concentrated sulfuric acid is added, and the mixture refluxed 3 hr. The mixture is concentrated, and the residue purified by silica chromatography eluting with 7:3 hexanes:ethyl acetate to afford the title compound as a pale yellow oil, 1.0 g, 69%. MS M++1 183. The structure is confirmed by 1H NMR spectroscopy.

1. temperatureat reflux 3 hr
2. concentrationThe mixture is concentrated
3. customproduct partitioned between 1M aqueous hydrochloric acid (50 mL) and ethyl acetate (3×75 mL)
4. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. addition2 mL concentrated sulfuric acid is added
8. temperaturethe mixture refluxed 3 hr
9. concentrationThe mixture is concentrated
10. customthe residue purified by silica chromatography
11. washeluting with 7:3 hexanes

ORD record

ord-b46e366d92ea48a69c2508f6f76f3d46

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153878B2