Ethanol → ethyl 4-mercaptobenzoate

Ethyl-4-mercaptobenzoate was prepared by treating 4-mercaptobenzoic acid (1.50 g, 9.73 mmol) with ethanol (97 mL) in the presence of catalytic concentrated sulfuric acid under a nitrogen atmosphere. The reaction was heated at reflux for three hours. The volume of the reaction was reduced to 10 mL under reduced pressure and then partitioned between water (100 mL) and ethyl acetate (100 mL). The aqueous layer was extracted with ethyl acetate (3×100 mL), and the combined organic solutions were washed with water (75 mL) and saturated aqueous sodium bicarbonate (2×75 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide an oil. The oil was dissolved in dichloromethane (100 mL), and the resulting solution was extracted with saturated aqueous sodium carbonate (3×100 mL). The combined extracts were washed with dichloromethane (3×50 mL) and then treated with concentrated hydrochloric acid to adjust to pH 7. The solution was then extracted with dichloromethane (3×100 mL), and the combined extracts were washed with water (50 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 1.23 g of ethyl-4-mercaptobenzoate as a colorless oil.

1. customEthyl-4-mercaptobenzoate was prepared
2. temperatureThe reaction was heated
3. temperatureat reflux for three hours
4. custompartitioned between water (100 mL) and ethyl acetate (100 mL)
5. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
6. washthe combined organic solutions were washed with water (75 mL) and saturated aqueous sodium bicarbonate (2×75 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customto provide an oil
11. extractionthe resulting solution was extracted with saturated aqueous sodium carbonate (3×100 mL)
12. washThe combined extracts were washed with dichloromethane (3×50 mL)
13. additiontreated with concentrated hydrochloric acid
14. extractionThe solution was then extracted with dichloromethane (3×100 mL)
15. washthe combined extracts were washed with water (50 mL)
16. dry with materialdried over magnesium sulfate
17. filtrationfiltered
18. concentrationconcentrated under reduced pressure

ORD record

ord-66baae2efdf34ede963b178cdda1b9e7

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07125890B2