Methanol → Methyl 4-chloro-3-mercapto-2-methylbenzoate
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[C:3]=1[SH:12].[CH3:13]O>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:13])=[O:7])=[C:4]([CH3:11])[C:3]=1[SH:12]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Under an atmosphere of nitrogen, 3.60 g (17.8 mmol) of 4-chloro-3-mercapto-2-methylbenzoic acid in 50 ml of absolute methanol and 1 ml of concentrated sulfuric acid were heated under reflux for 17 h. The mixture was freed from solvent, and the residue was taken up in water. After two extractions with ethyl acetate, the combined organic phases were dried, filtered under an atmosphere of nitrogen and freed from the solvent. What was isolated were 3.2 g of pure product.
Workup
- temperatureunder reflux for 17 h
- extractionAfter two extractions with ethyl acetate
- customthe combined organic phases were dried
- filtrationfiltered under an atmosphere of nitrogen
- customWhat was isolated
Sources & evidence
- ORD record
- ord-6d856e14df4a4ee1968b35f8c1ac6b7c
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943551B2
Reaction notes
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