Ethyl Acetate → p-Isobutylphenyl-p-tolyl-iodonium hexafluorophosphate

HRID 381204Notes

Reaction equation

HRID 381204 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5](C)=[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].[NH4+].[NH4+].[O-]S(OOS([O-])(=O)=O)(=O)=O.[F:31][P-:32]([F:37])([F:36])([F:35])([F:34])[F:33].[K+].[CH2:39](OC(=O)C)C>S(=O)(=O)(O)O.O>[F:31][P-:32]([F:37])([F:36])([F:35])([F:34])[F:33].[CH2:9]([C:13]1([I+:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:18]=[CH:17][C:16]([CH3:39])=[CH:15][CH2:14]1)[CH:10]([CH3:12])[CH3:11]

Participants

8

Reactant 5

HCID 8857Ethyl AcetateHCID 10870IsobutylbenzeneHCID 122074-IodotolueneHCID 62648Ammonium PersulfateHCID 23688904Potassium hexafluorophosphate

Product 1

HCID 86757504p-Isobutylphenyl-p-tolyl-iodonium hexafluorophosphateYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

45.22 g (0.21 mol) of 4-iodotoluene in 326 g of 75% sulfuric acid are introduced into a 750 ml flask having a reflux condenser, a thermometer, a stirrer and a nitrogen supply. 29.2 g (0.22 mol) of isobutylbenzene are then added, and the heterogeneous mixture is cooled to 1 0° C. 94.7 g (0.41 mol) of ammonium peroxodisulfate are added in portions so that the temperature does not exceed 15° C. The reaction mixture is stirred at room temperature for 5 hours. The reaction mixture is then added over the course of 40 minutes at 5-10° C. to a well stirred suspension of 38.18 g (0.21 mol) of potassium hexafluorophosphate in 600 ml of water and 500 ml of acetic acid ethyl ester. The mixture is maintained at room temperature for 1.5 hours, and the phases are separated. The organic phase is washed with water and 5% sodium hydrogen carbonate, and the solvent is removed in vacuo. 89 g (0.18 mol; 86%) of p-isobutylphenyl-p-tolyl-iodonium hexafluorophosphate are obtained in the form of a brownish resin. The product is purified further by chromatography (dichloromethane:ethanol 95:5 on SiO2) or by recrystallisation from chloroform/hexane.

Workup

  1. customdoes not exceed 15° C
  2. additionThe reaction mixture is then added over the course of 40 minutes at 5-10° C. to a well
  3. stirringstirred
  4. temperatureThe mixture is maintained at room temperature for 1.5 hours
  5. customthe phases are separated
  6. washThe organic phase is washed with water and 5% sodium hydrogen carbonate
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-2806e31d1d3f4240a17a9fffb2f6c017
Source dataset
uspto-grants-2001_10
Patent number
US06306555B1

Reaction notes

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