Hydrochloric Acid → 4,4'-Diiododiphenylsulfone

HRID 637812Notes

Reaction equation

HRID 637812 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](O)(=[O:17])=[O:16])=[CH:11][CH:10]=1.ClS(O)(=O)=O.Cl>O>[CH:11]1[C:12]([S:15]([C:5]2[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=2)(=[O:17])=[O:16])=[CH:13][CH:14]=[C:9]([I:8])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11575Iodobenzene2×HCID 24638Chlorosulfonic acidHCID 211026HCID 211026, compound

Product 1

HCID 2646894,4'-DiiododiphenylsulfoneYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 204 g (1 mole) of iodobenzene was added 312 g (1.1 moles) of 4-iodobenzenesulfonic acid and the mixture was cooled with water while 123 g of (1.1 moles) of chlorosulfonic acid was added thereto at about 10° to about 20° C. over a period of 1 hour. After the addition, the reaction system was stirred for 3 hours while being maintained at 20° to 30° C. The hydrochloric acid gas evolved during the reaction was continuously removed from the reaction system. After the completion of the reaction, about 400 ml of water was added to the reaction mixture and 20 g of (0.1 mole) of the unreacted iodobenzene was was recovered by distillation. Separation of the precipitate by filtration gave 123 g of 4,4'-diiododiphenylsulfone in 58% yield. M.P. 201° to 202° C. Purity of 99.6%.

Workup

  1. additionwas added
  2. additionAfter the addition
  3. temperaturewhile being maintained at 20° to 30° C
  4. customwas continuously removed from the reaction system
  5. customAfter the completion of the reaction, about 400 ml of water
  6. distillationwas was recovered by distillation
  7. customSeparation of the precipitate
  8. filtrationby filtration

Sources & evidence

ORD record
ord-9e3d4316f10d43748d3ff460f6f79d4c
Source dataset
uspto-grants-1985_12
Patent number
US04558161

Reaction notes

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