Chlorobenzene → 4,4'-Dichlorodiphenyl sulfone

HRID 637810Notes

Reaction equation

HRID 637810 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[S:9]([OH:12])(=O)=[O:10]>>[CH:4]1[C:5]([S:9]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:12])=[O:10])=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

3

Reactant 2

HCID 7964ChlorobenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 66254,4'-Dichlorodiphenyl sulfoneYield 25%

Procedure

To 112 g (1 mole) of chlorobenzene was added 123 g (1.1 moles) of chlorosulfonic acid at 10° to 20° C. After the addition, while being maintained at 20° to 30° C., the mixture was stirred for 3 hours to complete the reaction. A 0.1 mole quantity of the unreacted chlorobenzene was recovered in the same manner as in Example 1 and 32 g of 4,4'-dichlorodiphenylsulfone was obtained in 25% yield. M.P. 148.5° to 149.5° C. Purity of 99.8%.

Workup

  1. additionAfter the addition
  2. temperaturewhile being maintained at 20° to 30° C.
  3. customthe reaction
  4. customA 0.1 mole quantity of the unreacted chlorobenzene was recovered in the same manner as in Example 1

Sources & evidence

ORD record
ord-6dffa688d23c47a8994bd8c83483dbb6
Source dataset
uspto-grants-1985_12
Patent number
US04558161

Reaction notes

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