Sulfuric Acid → 4-t-Amylphenyliodonium sulfate

HRID 2179874Notes

Reaction equation

HRID 2179874 reaction equation
[C:1]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH2:4][CH3:5])([CH3:3])[CH3:2].[I:12]([O-])(=O)=O.[K+].C(OC(=O)C)(=O)C.[S:24](=[O:28])(=[O:27])([OH:26])[OH:25]>O.ClCCl>[S:24]([O-:28])([O-:27])(=[O:26])=[O:25].[C:1]([C:6]1[CH:7]=[CH:8][C:9]([IH+:12])=[CH:10][CH:11]=1)([CH2:4][CH3:5])([CH3:2])[CH3:3].[C:1]([C:6]1[CH:7]=[CH:8][C:9]([IH+:12])=[CH:10][CH:11]=1)([CH2:4][CH3:5])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 16295tert-AmylbenzeneHCID 23665710Potassium Iodate

Product 1

HCID 865852084-t-Amylphenyliodonium sulfate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

60 g of t-amylbenzene, 39.5 g of potassium iodate, 81 g of acetic anhydride and 170 ml of dichloromethane were mixed together. Then 66.8 g of conc. sulfuric acid was slowly added dropwise thereinto under ice-cooling. After stirring under ice-cooling for 2 hours, the mixture was stirred at room temperature for additional 10 hours. 500 ml of water was added to the liquid reaction mixture under ice-cooling and the mixture was extracted with dichloromethane. The organic phase was washed with sodium hydrogencarbonate and water and then concentrated to give (4-t-amylphenyl)iodonium sulfate. This sulfate was added to a solution of tetramethylammonium pentafluorobenzenesulfonate in excess. After adding 500 ml of water, the solution was extracted with dichloromethane. Then the organic phase was washed with a 5% aqueous solution of tetramethylammonium hydroxide and water and then concentrated to give di(4-t-amylphenyl)iodonium pentafluorobenzenesulfonate (III-1).

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling for 2 hours
  3. stirringthe mixture was stirred at room temperature for additional 10 hours
  4. temperaturecooling
  5. extractionthe mixture was extracted with dichloromethane
  6. washThe organic phase was washed with sodium hydrogencarbonate and water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-110eed1e33904c0f82318c5594c14baa
Source dataset
uspto-grants-2005_05
Patent number
US06887645B2

Reaction notes

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