Oxygen → HCID 86750013, compound

HRID 1901302Notes

Reaction equation

HRID 1901302 reaction equation
[F:1][P-:2]([F:7])([F:6])([F:5])([F:4])[F:3].[C:8]1([CH3:27])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S+:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O=O.[K+].O=O.C1(C)C=CC(S(Cl)(=O)=[O:40])=CC=1>CO>[F:1][P-:2]([F:7])([F:6])([F:5])([F:4])[F:3].[C:8]1([CH3:27])[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S+:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:40]

Participants

6

Reactant 4

HCID 977OxygenHCID 73974-Toluenesulfonyl chlorideHCID 6154112030-88-5HCID 23133109HCID 23133109, compound

Product 1

HCID 86750013HCID 86750013, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(Tolyl)diphenylsulphonium hexafluorophosphate (1.08 g, 2.57 mmol) is dissolved with stirring in methanol (40 ml). The resulting solution is cooled in an icewater bath while solid potassium superoxide (2.20 g, 31 mmol) is added slowly (with evolution of oxygen). After stirring for a further 15 minutes, a solution of p-toluenesulphonyl chloride (2.38 g, 12.5 mmol) in 30 ml methanol is added dropwise over 20-30 minutes. The reaction mixture is stirred for a further 30 min. After this time the mixture is filtered under vacuum. The residue is washed with methanol and the combined filtrate evaporated under reduced pressure. The resulting solid is slurried with water, filtered, and washed with water and ether, to give (tolyl)diphenylsulphoxonium hexafluorophosphate (0.6 g, 54 %) identical with authentic material.

Workup

  1. stirringThe reaction mixture is stirred for a further 30 min
  2. filtrationAfter this time the mixture is filtered under vacuum
  3. washThe residue is washed with methanol
  4. customthe combined filtrate evaporated under reduced pressure
  5. filtrationfiltered
  6. washwashed with water and ether

Sources & evidence

ORD record
ord-92574755fd0f46f2820f3fdb8cc4b229
Source dataset
uspto-grants-1996_11
Patent number
US05576461

Reaction notes

Loading…