Potassium Hydroxide → 4-Thiobenzonitrile

HRID 2295379Notes

Reaction equation

HRID 2295379 reaction equation
O(CC)C([S:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)=S.[OH-].[K+]>C(O)C>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([SH:4])=[CH:6][CH:7]=1)#[N:12]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 85976779HCID 85976779, compound

Product 1

HCID 5850584-ThiobenzonitrileYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ethyl 4-cyanophenyl xanthate was dissolved in ethanol (500 ml) and the solution was refluxed. Potassium hydroxide (112 g, 2 m) was added slowly to the resulting hot solution. Thereafter, the reaction mixture solution was refluxed for approximately three hours. The ethanol was distilled off from the reaction mixture and water (100 ml) was added. The reaction mixture was acidified with 6 N sulfuric acid and the reaction product was extracted with ether. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated and the reaction product was vacuum-distilled to yield 4-cyanobenzenethiol (20 g, 30%), bp 102°-103° C./2 mm.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureThereafter, the reaction mixture solution was refluxed for approximately three hours
  3. distillationThe ethanol was distilled off from the reaction mixture and water (100 ml)
  4. additionwas added
  5. extractionthe reaction product was extracted with ether
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. distillationthe reaction product was vacuum-distilled

Sources & evidence

ORD record
ord-da30e26ffca04a2e8382f2684c58acc6
Source dataset
uspto-grants-1984_01
Patent number
US04424372

Reaction notes

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