Water → 4-Ethylsulfonylbenzoic acid

HRID 2101416Notes

Reaction equation

HRID 2101416 reaction equation
[CH2:1]([S:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH3:2].S([O-])(O[O-])(=O)=[O:14].[K+].[K+].[OH2:21]>CO>[CH2:1]([S:3]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:14])=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 832314-(Ethylthio)benzoic acidHCID 10313463Potassium peroxymonosulphate

Product 1

HCID 1793674-Ethylsulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of 4-(ethylthio)benzoic acid (1 g, 5.5 mmol) in methanol (30 mL) at 0° C. under argon was added a solution of potassium peroxymonosulfate (6.8 g, 11 mmol) in water (30 mL). The resulted suspension was stirred at room temperature for 15 h. Methanol was evaporated under vacuum, the reaction mixture was diluted with water (30 mL), and the product was extracted with EtOAc (2×30 mL). The combined organic phase was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to obtain 910 mg of title compound as a white solid. HPLC/MS: retention time=1.695 min, [M+H]+=215.

Workup

  1. customMethanol was evaporated under vacuum
  2. additionthe reaction mixture was diluted with water (30 mL)
  3. extractionthe product was extracted with EtOAc (2×30 mL)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e341f2bd0754b7ebeee4c35d0e46636
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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