Methyl p-toluenesulfonate → Triphenylsulfonium p-toluenesulfonate

HRID 2057136

Reaction equation

HRID 2057136 reaction equation
C([O-])(=O)CC.[C:6]1([S+:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:25]1([CH3:36])[CH:30]=[CH:29][C:28]([S:31]([O:34]C)(=[O:33])=[O:32])=[CH:27][CH:26]=1>C(#N)C>[C:25]1([CH3:36])[CH:26]=[CH:27][C:28]([S:31]([O-:34])(=[O:32])=[O:33])=[CH:29][CH:30]=1.[C:19]1([S+:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 22995017Triphenylsulfanium propanoate

Product 1

HCID 21872467Triphenylsulfonium p-toluenesulfonateYield 113.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (5 ml) was added to triphenylsulfonium propionate (336 mg; 1.0 mmol) and methyl p-toluenesulfonate (204 mg; 1.1 mmol). The resultant mixture was refluxed for 5 hours while being stirred. The reaction mixture was cooled, and acetonitrile was removed through distillation under reduced pressure. The thus-obtained pale-yellow solid was washed with methylene chloride, and dried under vacuum, to thereby yield 492 mg of triphenylsulfonium p-toluenesulfonate (yield: 85%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customacetonitrile was removed through distillation under reduced pressure
  3. washThe thus-obtained pale-yellow solid was washed with methylene chloride
  4. customdried under vacuum

Sources & evidence

ORD record
ord-86ab4ec782df41ac9a0e1d4d1f457c04
Source dataset
uspto-grants-2008_02
Patent number
US07335787B2

Linked notes

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