Diethyl Ether → 1,1'-[1,3-Phenylenebis(sulfonyl-4,1-phenyleneoxy)]dibenzene

HRID 1834115Notes

Reaction equation

HRID 1834115 reaction equation
[C:1]1([S:11](Cl)(=[O:13])=[O:12])[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[CH2:15]([O:17][CH2:18][CH3:19])[CH3:16].[C:20]1([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[O:17]([C:18]1[CH:29]=[CH:28][C:27]([S:11]([C:1]2[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([C:30]3[CH:29]=[CH:28][C:27]([O:26][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:32][CH:31]=3)(=[O:9])=[O:8])[CH:2]=2)(=[O:13])=[O:12])=[CH:32][CH:19]=1)[C:15]1[CH:22]=[CH:21][CH:20]=[CH:25][CH:16]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 7583Diphenyl EtherHCID 962401,3-Benzenedisulfonyl dichloride

Product 1

HCID 203451351,1'-[1,3-Phenylenebis(sulfonyl-4,1-phenyleneoxy)]dibenzene

Conditions

Temperature
170 °C

Procedure

To a solution of 137.0 grams (0.498 mole) of m-benzenedisulfonyl chloride in 170 grams of diphenyl ether was added 1.0 gram of ferric chloride. The reaction was stirred at 170° C for 24 hours. After the reaction had cooled to room temperature, ethyl ether was added and the mixture was filtered and washed with water. The ether layer was separated, filtered, and dried over Na2SO4. Evaporation of the ether and distillation of diphenyl ether under reduced pressure afforded a crude solid. The crude product then was distilled under high vacuum (0.1mm) with an open flame. The distillate solidified upon cooling and was dissolved in 40 ml of chloroform and 800 ml of ethyl ether. A small amount of insoluble black residue was filtered from the solution. The addition of 800 ml of petroleum ether precipitated 160 grams (63%) of a white powder, mp 70°-75° C.

Workup

  1. temperatureAfter the reaction had cooled to room temperature
  2. filtrationthe mixture was filtered
  3. washwashed with water
  4. customThe ether layer was separated
  5. filtrationfiltered
  6. dry with materialdried over Na2SO4
  7. customEvaporation of the ether and distillation of diphenyl ether under reduced pressure
  8. customafforded a crude solid
  9. distillationThe crude product then was distilled under high vacuum (0.1mm) with an open flame
  10. temperatureupon cooling
  11. dissolutionwas dissolved in 40 ml of chloroform
  12. filtrationA small amount of insoluble black residue was filtered from the solution
  13. additionThe addition of 800 ml of petroleum ether
  14. customprecipitated 160 grams (63%) of a white powder, mp 70°-75° C.

Sources & evidence

ORD record
ord-01f6e14570374881b1e100fb835de5ed
Source dataset
uspto-grants-1978_01
Patent number
US04069205

Reaction notes

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