Chloroform → HCID 20458160, compound

HRID 544533Notes

Reaction equation

HRID 544533 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]1([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH3:42][S:43]([OH:46])(=[O:45])=[O:44].C(Cl)(Cl)Cl>>[CH3:42][S:43]([O-:46])(=[O:45])=[O:44].[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S+:14]([C:39]2[CH:40]=[CH:41][C:36]([O:35][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:37][CH:38]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 6395Methanesulfonic AcidHCID 7583Diphenyl EtherHCID 20458149HCID 20458149, compound

Product 1

HCID 20458160HCID 20458160, compoundYield 131.3%

Conditions

Temperature
100 °C

Procedure

A mixture of 42.51 g of bis-(4-phenoxyphenyl)sulfoxide, 187.23 g of diphenyl ether and 105.71 g of methane sulfonic acid was heated at 100° C. for 24 hours with stirring. The mixture was poured into 700 g of ice water and the resultant aqueous and sulfonium layers extracted four times with 200-ml portions of ether and five times with 200-ml portions of chloroform. The combined chloroform extracts were dried with magnesium sulfate and the chloroform removed on a rotary evaporator to give 91.66 g of tris-(4-phenoxyphenyl)sulfonium methane sulfonate with 1.7 equivalents of chloroform of solvation. This represents a 100 percent yield.

Workup

  1. extractionthe resultant aqueous and sulfonium layers extracted four times with 200-ml portions of ether and five times with 200-ml portions of chloroform
  2. dry with materialThe combined chloroform extracts were dried with magnesium sulfate
  3. customthe chloroform removed on a rotary evaporator

Sources & evidence

ORD record
ord-4a75f2f5e61c48639ec2c51e7c4ef29b
Source dataset
uspto-grants-1984_05
Patent number
US04451408

Reaction notes

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