Sulfuric Acid → 4-t-Amylphenyliodonium sulfate

HRID 1385855Notes

Reaction equation

HRID 1385855 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

Sixty grams of t-amylbenzene, 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 thereto under ice cooling. After stirring under ice cooling for 2 hours, the mixture was stirred at room temperature for 10 hours. To the reaction solution, 500 ml of water was added under ice cooling, and the resulting solution was extracted with dichloromethane. An organic phase was washed with sodium hydrogencarbonate and water, followed by concentration to obtain (4-t-amylphenyl)iodonium sulfate. This sulfate was added to an excess amount of the solution of tetramethylammonium pentafluorobnzenesulfonate. To this solution, 500 ml of water was added, and the resulting solution was extracted with dichloromethane. An organic phase was washed with a 5% aqueous solution of tetramethylammonium hydroxide and water, followed by concentration to obtain di(4-t-amylphenyl)iodonium pentafluorobenzenesulfonate.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 hours
  2. extractionthe resulting solution was extracted with dichloromethane
  3. washAn organic phase was washed with sodium hydrogencarbonate and water
  4. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-3675baf23f8846b69eb74d260aa431be
Source dataset
uspto-grants-2001_07
Patent number
US06265135B1

Reaction notes

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