Hydrogen Peroxide → alpha-Methylsulfonyl(2-thienyl)acetic acid
Reaction equation
[CH3:1][S:2][CH:3]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[C:4]([OH:6])=[O:5].OO.[OH2:14].C(Cl)Cl.C[OH:19]>C1C=CC=CC=1.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:1][S:2]([CH:3]([C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[C:4]([OH:6])=[O:5])(=[O:19])=[O:14]Participants
Procedure
α-Methylthio(2-thienyl)acetic acid (1.731 g) was dissolved in 20 ml of methanol, and 10 mg of sodium tungstate and 3.34 ml of a 30% aqueous solution of hydrogen peroxide were added. The mixture was stirred at room temperature for 70 hours. To the reaction mixture were added 30 ml of water and 30 ml of methylene chloride. The organic layer was separated. The aqueous layer was extracted four times with 30 ml of methylene chloride. The resulting organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to afford yellow crystals. The crystals were dissolved in benzene, and the insoluble matter was separated by filtration. The residue was concentrated under reduced pressure. Recrystallization of the resulting yellow crystals from benzene/n-hexane afforded 997 mg of α-methylsulfonyl(2-thienyl)acetic acid as pale yellow crystals.
Workup
- customThe organic layer was separated
- extractionThe aqueous layer was extracted four times with 30 ml of methylene chloride
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customto afford yellow crystals
- customthe insoluble matter was separated by filtration
- concentrationThe residue was concentrated under reduced pressure
- customRecrystallization of the resulting yellow crystals from benzene/n-hexane
Sources & evidence
- ORD record
- ord-26874c243ea74ecfb463519e36d0a369
- Source dataset
- uspto-grants-1979_01
- Patent number
- US04137406
Reaction notes
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