Bromopinacolone → SBB058976

HRID 2226817Notes

Reaction equation

HRID 2226817 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+]>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

4

Reactant 2

HCID 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-dimethylbutan-2-one (33.3 g, 0.19 mole) in dimethylsulfoxide (330 ml), sodium p-toluenesulfinate (34.9 g, 0.20 mole) was added in a small portion at 30°-40° C., and stirring was continued at 60°-70° C. for 18 hours. The resultant mixture was poured into ice-cold H2O (2 l), the precipitate was filtered by suction, washed with H2O and dried to give 41.6 g of 1-(p-toluenesulfonyl)-3,3-dimethylbutan-2-one as white crystals.

Workup

  1. filtrationthe precipitate was filtered by suction
  2. washwashed with H2O
  3. customdried

Sources & evidence

ORD record
ord-2444b0984a314c35bf66e35b76e5ea89
Source dataset
uspto-grants-1994_09
Patent number
US05350660

Reaction notes

Loading…