Chloroacetone → (p-Tolylsulphonyl)acetone

HRID 1864757

Reaction equation

HRID 1864757 reaction equation
O.O.[C:3]1([CH3:12])[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[Na+].Cl[CH2:15][C:16](=[O:18])[CH3:17].O.C1C=CC=CC=1.CC(C)=O>C(OCC)(=O)C.CCCCCCC>[C:3]1([CH3:12])[CH:8]=[CH:7][C:6]([S:9]([CH2:15][C:16](=[O:18])[CH3:17])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 23678556Sodium toluene-4-sulphinate dihydrateHCID 68819625Water benzene acetone

Product 1

HCID 79327(p-Tolylsulphonyl)acetoneYield 95%

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

was prepared according to Crandall et al. J. Org. Chem. 1985, (8) 50, 1327-1329 from sodium p-toluenesulfinate dihydrate (4.2 g, 18 mmol), chloroacetone (1.0 mL, 12 mmol), n-tetrabutylammonium bromide (0.30 g) and water-benzene-acetone 4:3:3 (10 mL). Work-up and chromatography on silica of the crude using ethyl acetate/n-heptane (1:3 through 1:2) as eluent gave 2.4 g (95%) of the title product as an oil which crystallised on standing in the fridge.

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-453fc890120742d0a94fafc1763fd2c5
Source dataset
uspto-grants-2009_12
Patent number
US07625934B2

Linked notes

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