Methanol → 4-(Methanesulfonyl)-3-nitrobenzoic acid

HRID 1785330Notes

Reaction equation

HRID 1785330 reaction equation
CS[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].O[O:16][S:17]([O-:19])=O.[K+].[CH3:21]O>O>[CH3:21][S:17]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])(=[O:19])=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 5425314-Methylthio-3-nitrobenzoic acidHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 27238714-(Methanesulfonyl)-3-nitrobenzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

4-Methylsulfanyl-3-nitro-benzoic acid (1 g, 4.69 mmole) was dissolved in methanol (25 ml) and cooled to 5° C. A solution of Oxone® (5.8 g) in water (20 ml) was added portionwise at the same temperature. The reaction mixture was allowed to stir overnight at ambient temperature, methanol was removed under reduced pressure. The suspension was diluted with water and the solid was filtered off and dried in vacuum to provide 4-Methanesulfonyl-3-nitro-benzoic acid in 89% yield (960 mg). ESI-MS: 246.

Workup

  1. custommethanol was removed under reduced pressure
  2. additionThe suspension was diluted with water
  3. filtrationthe solid was filtered off
  4. customdried in vacuum

Sources & evidence

ORD record
ord-78753cfe6dbd453bb7a910a347da8ed0
Source dataset
uspto-grants-2009_03
Patent number
US07504410B2

Reaction notes

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