Hydrogen Peroxide → Methyl phenyl sulfone

HRID 385236Notes

Reaction equation

HRID 385236 reaction equation
[C:1]1([S:7]([CH3:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:10]O>O>[C:1]1([S:7]([CH3:9])(=[O:10])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 14516Methyl phenyl sulfoxide

Product 1

HCID 18369Methyl phenyl sulfoneYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

A complex (4) (1.9 mg, 1 mol %) was weighed out in a Schlenk flask, to which racemic phenylmethylsulfoxide (28 mg, 0.2 mmol) was added. Water (0.5 mL) was added, followed by stirring for 10 minutes at 20° C. A 30% hydrogen peroxide solution (9 μL, 0.4 eq) was added, followed by stirring the resultant mixture for 3 hours at room temperature. To the reaction mixture, water (5 mL) was added, followed by extraction using ethyl acetate. An organic phase was dried over anhydrous sodium sulfate, followed by filtration and then it was concentrated under reduced pressure. By purifying the concentrate using silica gel column chromatography (ethyl acetate), 6.5 mg (21% yield) of phenylmethylsulfone was obtained, and 22.1 mg of phenylmethylsulfoxide (79%) was recovered. Optical purity was determined to be 12% ee for a S form after measured by HPLC analysis.

Workup

  1. additionwas added
  2. extractionfollowed by extraction
  3. dry with materialAn organic phase was dried over anhydrous sodium sulfate
  4. filtrationfollowed by filtration
  5. concentrationit was concentrated under reduced pressure
  6. customBy purifying the concentrate

Sources & evidence

ORD record
ord-480bf3c7f2aa4797a30f8346a5d12db8
Source dataset
uspto-grants-2013_02
Patent number
US08367871B2

Reaction notes

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