Sulfuric Acid → (4-Methylphenyl)(4'-isobutylphenyl)iodonium hydrogensulfate

HRID 585032Notes

Reaction equation

HRID 585032 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH2:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:10]([CH3:12])[CH3:11].[S:19](=[O:23])(=[O:22])([OH:21])[OH:20].[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O>O>[S:19]([O-:23])([OH:22])(=[O:21])=[O:20].[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([I+:1][C:16]2[CH:17]=[CH:18][C:13]([CH2:9][CH:10]([CH3:12])[CH3:11])=[CH:14][CH:15]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 10870IsobutylbenzeneHCID 122074-IodotolueneHCID 62648Ammonium Persulfate

Product 1

HCID 86591397(4-Methylphenyl)(4'-isobutylphenyl)iodonium hydrogensulfate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

11.9 g (54.8 mmol) of 4-iodotoluene and 9.2 g (68.5 mmol) of isobutylbenzene are added dropwise to a solution of 35 ml of conc. sulfuric acid and 22 ml of water under cooling by an ice bath. 25 g of ammonium peroxodisulfate are added by portions to the solution under cooling by an ice-salt bath, keeping the temperature below 0° C. for 1 hour. The reaction mixture is stirred overnight and the temperature is gradually raised to room temperature during the course of the reaction. After cooling the reaction mixture by ice an bath, 118 ml of water are added. The product is extracted with methylene chloride, and the organic layer is washed with water, dried over MgSO4, and concentrated, yielding (4-methylphenyl)(4′-isobutylphenyl)iodonium hydrogensulfate as a brown solid. The crude (4-methylphenyl)(4′-isobutylphenyl)iodonium hydrogensulfate is used in the next step without further purification.

Workup

  1. temperatureunder cooling by an ice bath
  2. temperatureunder cooling by an ice-salt bath
  3. customthe temperature below 0° C.
  4. customfor 1 hour
  5. additionare added
  6. extractionThe product is extracted with methylene chloride
  7. washthe organic layer is washed with water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-15904a8f836840019e4a85ac08f2627a
Source dataset
uspto-grants-2005_08
Patent number
US06929896B2

Reaction notes

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