Hydrochloric Acid → 4-Chloro-3-ethylthio-2-methylbenzoic acid

3.71 g (11.3 mmol) of cesium carbonate were added to 1.10 g (5.42 mmol) of 4-chloro-3-mercapto-2-methylbenzoic acid in 20 ml of acetonitrile. The reaction mixture was stirred at RT for 10 min, and 1.02 g (6.51 mmol) of iodoethane were then slowly added dropwise. The reaction mixture was then stirred at RT for 16 h. The solvent was then removed, and a mixture of 20 ml of methanol and 2 ml of 20% strength aqueous sodium hydroxide solution was then added to the reaction mixture. For the hydrolysis of the ethyl ester formed, the mixture was stirred at RT for 16 h and then freed from the solvents. The residue was taken up in water and acidified with diluted HCl, and the mixture was stirred at RT for 10 min and then filtered. The residue was washed with water and sucked dry. 1.15 g of clean product were isolated.

1. stirringThe reaction mixture was then stirred at RT for 16 h
2. customThe solvent was then removed
3. additiona mixture of 20 ml of methanol and 2 ml of 20% strength aqueous sodium hydroxide solution
4. additionwas then added to the reaction mixture
5. customFor the hydrolysis of the ethyl ester
6. customformed
7. stirringthe mixture was stirred at RT for 16 h
8. stirringthe mixture was stirred at RT for 10 min
9. filtrationfiltered
10. washThe residue was washed with water
11. customsucked dry

ORD record

ord-febf48003a774154aad8ad5c33643acd

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114816B2