Acetic Acid → 2-Methyl-4-methylsulfonyl-3-(4-methylsulfonylphenyl)benzoic acid

HRID 1386882Notes

Reaction equation

HRID 1386882 reaction equation
[CH3:1][C:2]1[C:10]([C:11]2[CH:16]=[CH:15][C:14](SC)=[CH:13][CH:12]=2)=[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OO.[C:25](O)(=O)C.[S:29](=[O:32])([OH:31])[O-].[Na+]>O>[CH3:1][C:2]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([S:29]([CH3:25])(=[O:32])=[O:31])=[CH:13][CH:12]=2)=[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 23665763Sodium BisulfiteHCID 538945492-Methyl-4-methylsulfonyl-3-(4-methylthiophenyl)benzoic Acid

Product 1

HCID 211831432-Methyl-4-methylsulfonyl-3-(4-methylsulfonylphenyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.2 g (6.5 mmol) of 2-methyl-4-methylsulfonyl-3-(4-methylthiophenyl)benzoic acid, 2.2 mL (19.6 mmol) of 30 percent hydrogen peroxide, and 25 mL of acetic acid was heated to 80° C. with stirring for 1 hour and was then allowed to stand overnight. The mixture was diluted with water, treated with sodium bisulfite, and then extracted with a mixture of ether and ethyl acetate. The extract was concentrated by evaporation under reduced pressure and the residue was diluted with dichloromethane. The resulting mixture was filtered and the solids that were collected were washed with ethyl acetate. The filtrate was found to contain only about 0.5 g of impure product and was discarded. The solids were dissolved (a slow process) in a mixture of ethyl acetate and water and the organic phase was separated and concentrated by evaporation under reduced pressure. The resulting solid residue was diluted with hexane and the insoluble solids were recovered by filtration and dried to obtain 2.1 g (88 percent of theory) of the title compound as a white powder melting at 214-215° C.

Workup

  1. waitto stand overnight
  2. extractionextracted with a mixture of ether and ethyl acetate
  3. concentrationThe extract was concentrated by evaporation under reduced pressure
  4. additionthe residue was diluted with dichloromethane
  5. filtrationThe resulting mixture was filtered
  6. customthe solids that were collected
  7. washwere washed with ethyl acetate
  8. dissolutionThe solids were dissolved (a slow process)
  9. additionin a mixture of ethyl acetate and water
  10. customthe organic phase was separated
  11. concentrationconcentrated by evaporation under reduced pressure
  12. additionThe resulting solid residue was diluted with hexane
  13. filtrationthe insoluble solids were recovered by filtration
  14. customdried

Sources & evidence

ORD record
ord-ebf80b1a8530491b8c30396748059ab6
Source dataset
uspto-grants-2001_07
Patent number
US06265606B1

Reaction notes

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