Hydrogen Peroxide → HCID 20306489, compound

HRID 1732451Notes

Reaction equation

HRID 1732451 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([N:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].OO.S([O-])([O-])(=[O:21])=S.[Na+].[Na+].[OH2:26]>CO.O.O.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:1][S:2]([CH:3]([C:8]1[CH:9]=[CH:10][C:11]([N:14]([CH3:16])[CH3:15])=[CH:12][CH:13]=1)[C:4]([O:6][CH3:7])=[O:5])(=[O:21])=[O:26]

Participants

7

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 962WaterHCID 24477Sodium ThiosulfateHCID 20306504HCID 20306504, compound

Product 1

HCID 20306489HCID 20306489, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 150191Sodium Tungstate DihydrateCatalystHCID 887MethanolSolvent

Procedure

Methyl α-methylthio(p-dimethylaminophenyl)acetate (105 mg) was dissolved in 10 ml of methanol, and 8.2 mg of sodium tungstate dihydrate and 0.6 ml of a 30% aqueous solution of hydrogen peroxide were added. The mixture was stirred at room temperature for 60 hours. The remaining hydrogen peroxide was decomposed with sodium thiosulfate, and 20 ml of water was added to the mixture. It was then extracted three times with 10 ml of methylene chloride. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Recrystallization of the residue from methanol afforded 76 mg of methyl α-methylsulfonyl(p-dimethylaminophenyl)acetate in a yield of 63.5%.

Workup

  1. additionwas added to the mixture
  2. extractionIt was then extracted three times with 10 ml of methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customRecrystallization of the residue from methanol

Sources & evidence

ORD record
ord-dac99df9e3874050b98135aeab106cd8
Source dataset
uspto-grants-1980_12
Patent number
US04237298

Reaction notes

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