Methanol → 2-Chloro-5-(methylsulphonyl)benzoic acid
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8](SC)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O[O:14][S:15]([O-:17])=O.[K+].[CH3:19]O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:15]([CH3:19])(=[O:17])=[O:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]Participants
4
Procedure
To 99 mmol 2-chloro-5-(methylthio) benzoic acid in 400 ml methanol at 0° C. 296 mmol oxone® was added, and the mixture was allowed to stir at RT for 3.5 h. The precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was extracted 3× with 400 ml ethyl acetate, and the combined organic phases washed 2× with 300 ml 1N HCl and with 300 ml saturated aqueous NaCl solution and dried with MgSO4. Evaporation under reduced pressure yielded the title compound.
Workup
- customat 0° C
- filtrationThe precipitate was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- extractionThe residue was extracted 3× with 400 ml ethyl acetate
- washthe combined organic phases washed 2× with 300 ml 1N HCl
- dry with materialwith 300 ml saturated aqueous NaCl solution and dried with MgSO4
- customEvaporation under reduced pressure
Sources & evidence
- ORD record
- ord-a9964e7ee92b40a2b3ac9ca0e57a121d
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07319099B2
Reaction notes
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