Water → 4-Ethylsulfonylbenzoic acid

HRID 271473

Reaction equation

HRID 271473 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 saturated aqueous NaCl, 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 saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b72705c2182d4eceafbc4e79c2daa821
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Linked notes

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