Sulfuric Acid → 4-t-Amylphenyliodonium sulfate

HRID 1635786Notes

Reaction equation

HRID 1635786 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

t-Amylbenzene (60 g), 39.5 g of potassium iodate, 81 g of acetic anhydride and 170 ml of dichloromethane were mixed, and 66.8 g of concentrated sulfuric acid was slowly added dropwise thereto under ice cooling. After stirring for 2 hours under ice cooling, the mixture was stirred at room temperature for 10 hours. Then, 500 ml of water was added to the reaction solution under ice cooling, and the resulting solution was extracted with dichloromethane. The organic phase was washed with sodium hydrogen carbonate and water, and then concentrated to obtain di (4-t-amylphenyliodonium sulfate. To a solution of tetramethylammonium pentafluorobenzenesulfonate in excess the obtained sulfate was added. Then, 500 ml of water was added to the solution, and 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 obtain di(4-t-amylphenyl)iodonium penta-fluorobenzenesulfonate (III-1).

Workup

  1. stirringthe mixture was stirred at room temperature for 10 hours
  2. extractionthe resulting solution was extracted with dichloromethane
  3. washThe organic phase was washed with sodium hydrogen carbonate and water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4064cd6803d84205a836c83ab266dd35
Source dataset
uspto-grants-2003_01
Patent number
US06511783B1

Reaction notes

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