p-Toluenesulfonic acid monohydrate → HCID 22726273, compound

HRID 2085904Notes

Reaction equation

HRID 2085904 reaction equation
FC(F)(F)S([O-])(=O)=O.[C:9]1([S+:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36]([OH:39])(=[O:38])=[O:37])=[CH:32][CH:31]=1>CO.C[N+](C)(C)C.[Cl-]>[C:30]1([CH3:40])[CH:31]=[CH:32][C:33]([S:36]([O-:39])(=[O:37])=[O:38])=[CH:34][CH:35]=1.[C:23]1([S+:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22726283HCID 22726283, compound

Product 1

HCID 22726273HCID 22726273, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 887MethanolSolvent

Procedure

In aqueous methanol solution was dissolved 18.8 g (44 mmole) of the resulting diphenyl-o-methylphenylsulfonium trifluoromethanesulfonate and passed through an activated strong base type anion exchange resin (Amberlite IRA-900; mfd. by Organo Corporation.). To the eluting solution was added 10.0 g (53 mmole) of p-toluenesulfonic acid monohydrate, followed by allowing a reaction to take place at room temperature for 1 hour with stirring. After the reaction, the solvent was removed and the residue was dissolved in 200 ml of methylene chloride, washed with water three times and concentrated under reduced pressure to give 17.2 g (Yield: 91%) of diphenyl-o-methylphenylsulfonium p-toluenesulfonate as white crystal.

Workup

  1. customa reaction
  2. customat room temperature
  3. customfor 1 hour
  4. customAfter the reaction
  5. customthe solvent was removed
  6. dissolutionthe residue was dissolved in 200 ml of methylene chloride
  7. washwashed with water three times
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2cec895de4194964bed46b0647d60624
Source dataset
uspto-grants-2004_04
Patent number
US06723483B1

Reaction notes

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