Acetic Acid → (4-Octyloxyphenyl)phenyliodonium tosylate

HRID 129653Notes

Reaction equation

HRID 129653 reaction equation
O[C:2]1[C:3]([O:9][S:10]([C:13]2[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[C:4]([I:8])[CH:5]=[CH:6][CH:7]=1.[C:20]1([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(#N)C.C(O)(=O)C>O>[S:10]([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)([O-:12])(=[O:11])=[O:9].[CH2:27]([O:26][C:20]1[CH:21]=[CH:22][C:23]([I+:8][C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=2)=[CH:24][CH:25]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 6342AcetonitrileHCID 74558Octyl phenyl etherHCID 21918218Hydroxy tosyloxy iodobenzene

Product 1

HCID 22131423(4-Octyloxyphenyl)phenyliodonium tosylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

22.2 g (or 0.057 mol) of hydroxy-tosyloxyiodobenzene, 9 g (or 0.04 mol) of n-octyl phenyl ether, 5 ml of acetonitrile and 1.5 ml of acetic acid were charged into a 250 ml Erlenmeyer flask equipped with a magnetic stirrer bar. This mixture was stirred and was heated to a temperature of 40° C. for 2 hours, 30 minutes. 1.5 ml of glacial acetic acid was then added and the mixture was then maintained for 5 hours at 40° C. The reaction mixture was permitted to cool and 150 ml of water were added while stirring vigorously. This mixture was then stirred for 12 hours at room temperature and was then separated. The organic phase was washed several times with water, until a yellow precipitate appeared. This solid was recovered by filtration, was washed with 50 ml of ether and was then dried under vacuum at a temperature of 45° C.

Workup

  1. customequipped with a magnetic stirrer bar
  2. temperaturethe mixture was then maintained for 5 hours at 40° C
  3. temperatureto cool
  4. stirringwhile stirring vigorously
  5. stirringThis mixture was then stirred for 12 hours at room temperature
  6. customwas then separated
  7. washThe organic phase was washed several times with water
  8. filtrationThis solid was recovered by filtration
  9. washwas washed with 50 ml of ether
  10. customwas then dried under vacuum at a temperature of 45° C.

Sources & evidence

ORD record
ord-10c8a5c162f843e7a8058afe2b6f543d
Source dataset
uspto-grants-1995_11
Patent number
US05468902

Reaction notes

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