Hydrochloric Acid → 3-Mercapto-2-methylbenzoic acid
Reaction equation
C(OC([S:6][C:7]1[C:8]([CH3:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=S)C.[OH-].[Na+].Cl>>[SH:6][C:7]1[C:8]([CH3:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11]Participants
4
Procedure
3-{[(ethyloxy)carbonothioyl]thio}-2-methylbenzoic acid (270 mg, 1.05 mmol) in a 1N aqueous sodium hydroxide solution (3 mL) was stirred at reflux for 15 hours. The mixture was cooled to room temperature and the pH was adjusted to 2 using concentrated aqueous hydrochloric acid. The aqueous mixture was extracted twice using dichloromethane and the combined organic solutions were washed with brine, then dried over anhydrous sodium sulfate. Filtration and concentration afforded 180 mg, 1.05 mmol (99%) of 3-mercapto-2-methylbenzoic acid. 1H NMR (400 MHz, CDCl3): 7.87 (d, 1H), 7.47 (d, 1H), 7.16-7.11 (m, 1H), 3.43 (s, 1H), 2.62 (s, 3H).
Workup
- temperatureat reflux for 15 hours
- extractionThe aqueous mixture was extracted twice using dichloromethane
- washthe combined organic solutions were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- filtrationFiltration and concentration
Sources & evidence
- ORD record
- ord-0661084640784150911a09b26efd9e57
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012956B2
Reaction notes
Loading…