Hydrogen Peroxide → 4-(Methylsulfonyl)aniline
Reaction equation
[OH2:1].[CH3:2][S:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[OH:11]O>C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:2][S:3]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)(=[O:11])=[O:1]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
67 mg of Na2WO4, 8 drops of acetic acid and 19 mL of H2O were introduced into a flask and heated to 65° C. Then, 19 mL (153 mmol) of 4-methylthioaniline was added followed by the dropwise addition of 34.5 mL (337 mmol) of H2O2. The mixture was stirred at 65° C. for 1.5 h and, after cooling, 800 mL of 1N HC and 500 mL of CHCl3 was added. The layers were separated and the aqueous phase was washed with more CHCl3. The aqueous phase was then basified with 25% NaOH and extracted with CHCl3. The organic phase was washed with brine and dried over MgSO4. The solvent was removed, yielding 19.80 g of the product as a white solid (75% yield).
Workup
- temperatureafter cooling
- customThe layers were separated
- washthe aqueous phase was washed with more CHCl3
- extractionextracted with CHCl3
- washThe organic phase was washed with brine
- dry with materialdried over MgSO4
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-365baee497e543019cdc5e24553a0bb6
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06743816B2
Reaction notes
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