p-Chlorothiophenol → [p-(p-Chlorophenylthio)phenyl]acetic Acid

HRID 1863268Notes

Reaction equation

HRID 1863268 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[K+].I[C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=1>O.[Cu]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=[O:20])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7815p-ChlorothiophenolHCID 14797Potassium HydroxideHCID 1372144-Iodophenylacetic acid

Product 1

HCID 12531841[p-(p-Chlorophenylthio)phenyl]acetic Acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

A solution of 6.0 g of 4-chlorothiophenol and 8.0 g of potassium hydroxide in 80 ml of water is heated to 50° C. and 0.8 g of copper powder and 10.4 g of 4-iodophenylacetic acid are added. The mixture is heated to reflux and maintained at reflux overnight. The mixture is then cooled and filtered. The filtrate is acidified with concentrated HCl to give a white solid which, on recrystallization from methanol, yields cream colored plates, mp 135°-140° C. A sample is recrystallized from chloroform-hexane to give white plates, mp 144.5°-148° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux overnight
  5. temperatureThe mixture is then cooled
  6. filtrationfiltered
  7. customto give a white solid which
  8. customon recrystallization from methanol
  9. customyields cream colored plates, mp 135°-140° C
  10. customA sample is recrystallized from chloroform-hexane
  11. customto give white plates, mp 144.5°-148° C.

Sources & evidence

ORD record
ord-bd14d5c9155641048c61f167eae7788f
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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