Benzenesulfonyl chloride → 2,4-Dimethyldiphenylsulfone

HRID 505982Notes

Reaction equation

HRID 505982 reaction equation
CCCCN1C=[N+](C)C=C1.[C:11]1([CH3:18])[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[CH:12]=1.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.N(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[Zn+2]>[CH3:18][C:11]1[CH:16]=[CH:15][C:14]([S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])=[C:13]([CH3:17])[CH:12]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chloride2×HCID 7929M-XyleneHCID 27341621-Butyl-3-methylimidazolium

Product 1

HCID 5210842,4-DimethyldiphenylsulfoneYield 99%

Reagents, catalysts & solvents 1

HCID 131725279Zinc(II) bis-triflimideCatalyst

Procedure

Zinc(II) bis-triflimide (0.062 g, 1 mol %) was dissolved in [bmim] [NTf2] (1.0 g) in a round-bottomed flask equipped with a magnetic stirrer and reflux condenser and m-xylene (2.12 g, 20 mmol) and benzene sulfonyl chloride (1.76 g, 10 mmol) were added. The mixture was heated under reflux for 18 hours and was analysed by gas chromatographic analysis as in previous examples. All the benzene sulfonyl chloride had reacted and mostly 2,4-dimethyldiphenylsulfone had formed (yield=99%, 20:1 isomer ratio {by NMR}). The major product is shown below, the structure of the minor isomer is not known but is believed to be the 2,6-dimethyl isomer.

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 18 hours

Sources & evidence

ORD record
ord-2dee0ecbec004775a240ba780a38d605
Source dataset
uspto-grants-2010_08
Patent number
US07781625B2

Reaction notes

Loading…