Hydrogen Peroxide → 1-(Isopropylsulfonyl)propan-2-one

HRID 1378903Notes

Reaction equation

HRID 1378903 reaction equation
[CH3:1][CH:2]([SH:4])[CH3:3].[OH-:5].[K+].Cl[CH2:8][C:9](=[O:11])[CH3:10].[OH:12]O>C(O)C.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[CH3:1][CH:2]([S:4]([CH2:8][C:9]([CH3:10])=[O:11])(=[O:12])=[O:5])[CH3:3]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 63642-PropanethiolHCID 6571ChloroacetoneHCID 14797Potassium Hydroxide

Product 1

HCID 229086371-(Isopropylsulfonyl)propan-2-oneYield 71.9%

Reagents, catalysts & solvents 2

HCID 26052Sodium tungstateCatalystHCID 702EthanolSolvent

Procedure

To 2-propanethiol (12.2 g, 0.16 mole), a solution of potassium hydroxide (11.5 g, 0.174 mole) in ethanol (100 ml) was added dropwise at 15° C. or lower, and continued to stir at the same temperature for 24 hours. Then chloroacetone (23.1 g, 0.25 mole) was added dropwise at 10°-15° C., and reacted with stirring at 20° C. for 4 hours. To this mixture, sodium tungstate (0.8 g) was added, 30% hydrogen peroxide (36 g, 0.32 mole) was added dropwise at 45°-55° C., and reacted with stirring at room temperature for 14 hours. The reaction mixture was extracted with methylene chloride (200 ml). The organic layer was washed with H2O, dried over anhydrous MgSO4 and evaporated to give 18.9 g of residual crude 1-(1-methylethylsulfonyl) acetone as a brownish yellow oil.

Workup

  1. customreacted
  2. stirringwith stirring at 20° C. for 4 hours
  3. customreacted
  4. stirringwith stirring at room temperature for 14 hours
  5. extractionThe reaction mixture was extracted with methylene chloride (200 ml)
  6. washThe organic layer was washed with H2O
  7. dry with materialdried over anhydrous MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-67065dbe61c945c1b1d7d376cd5cded0
Source dataset
uspto-grants-1997_09
Patent number
US05670299

Reaction notes

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