Sulfuric Acid → Bis(4-methylphenyl)iodanium chloride

HRID 2234153Notes

Reaction equation

HRID 2234153 reaction equation
S(=O)(=O)(O)O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[NH4+].[NH4+].[I:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1.[Cl-:26].[Na+]>O.C1(C)C=CC=CC=1.C(O)(=O)C>[Cl-:26].[C:22]1([CH3:25])[CH:23]=[CH:24][C:19]([I+:18][C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 122074-IodotolueneHCID 62648Ammonium Persulfate

Product 1

HCID 3084300Bis(4-methylphenyl)iodanium chloride

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

A reaction vessel was fed with 6.35 g of ice and 20 g of sulfuric acid, and cooled to 20° C. Then, 30 g of glacial acetic acid was fed, 41 g of ammonium persulfate were added at 25° C. or lower. After cooling this mixture to 15° C., a mixture of 21.8 g of 4-iodo toluene and 36.8 g of toluene were added dropwise over 2 hours, while keeping the temperature of the solution at 20° C. After stirring at 20° C. for 15 hours, 135 g of water with 35% in mass of sodium chloride was added, the deposited solid product was filtered and washed with saturated sodium chloride water, followed by water washing. After further washing with toluene and hexane, the solid was dried under reduced pressure. By recrystallization from acetone, 15.9 g of di-p-tolyl iodonium chloride were obtained as pale yellow crystals (yield: 46%).

Workup

  1. temperatureAfter cooling this mixture to 15° C.
  2. additionwere added dropwise over 2 hours
  3. customat 20° C
  4. filtrationthe deposited solid product was filtered
  5. washwashed with saturated sodium chloride water
  6. washAfter further washing with toluene and hexane
  7. customthe solid was dried under reduced pressure
  8. customBy recrystallization from acetone

Sources & evidence

ORD record
ord-efd12d2f19c04300b7549bdf737a661c
Source dataset
uspto-grants-2010_05
Patent number
US07709598B2

Reaction notes

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