Water → SBB058976

HRID 129374Notes

Reaction equation

HRID 129374 reaction equation
Br[CH2:2][C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[C:9]1([CH3:18])[CH:14]=[CH:13][C:12]([S:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.[Na+].O>CS(C)=O>[C:9]1([CH3:18])[CH:14]=[CH:13][C:12]([S:15]([CH2:2][C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21642BromopinacoloneHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 264831SBB058976Yield 86.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-bromo-3,3-dimethyl-2-butanone (33.3 g, 0.19 mole) in dimethylsulfoxide (330 ml), sodium p-toluenesulfinate (34.9 g, 0.20 mole) was added at 30°-40° C., and reacted with stirring at 60°-70° C. for 18 hours. The reaction mixture was poured into cold H2O (2 liter). The precipitate was filtered, washed with H2O and dried to afford 41.6 g of 1-(p-toluenesulfonyl)-3,3-dimethyl-2-butanone as white crystals. m.p. 119°-122° C.

Workup

  1. customreacted
  2. filtrationThe precipitate was filtered
  3. washwashed with H2O
  4. customdried

Sources & evidence

ORD record
ord-f677522836dd4ffe9a8025e93cd19288
Source dataset
uspto-grants-1995_11
Patent number
US05468589

Reaction notes

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