Phenol → 2-Phenoxypropanenitrile

HRID 1288229Notes

Reaction equation

HRID 1288229 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:15]([CH3:18])[C:16]#[N:17].[I-].[K+]>CC(CC)=O.O>[O:7]([CH:15]([CH3:18])[C:16]#[N:17])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5192252-Chloropropionitrile

Product 1

HCID 190944362-Phenoxypropanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A mixture of phenol (18.8 g.) and anhydrous potassium carbonate (25 g.) in dry ethyl methyl ketone (35 ml.) was stirred and heated to reflux, during the dropwise addition of a solution of 2-chloropropionitrile (19.7 g.) in dry ethyl methyl ketone (15 ml.) containing finely-powdered potassium iodide (0.5 g.). The addition took 20 minutes. Stirring and heating were continued for a total of 2 hours after which the mixture was cooled, poured into water (200 ml.) and extracted with ether (200, 75 and 75 ml.). The combined ether extract was washed several times with 2N-sodium hydroxide to remove phenol, dried over anhydrous sodium sulphate, and evaporated. The residue was distilled under water-pump vacuum to give pure 2-phenoxypropionitrile, b.p. 117°-118°/13 mm.

Workup

  1. temperatureheated
  2. additionThe addition
  3. stirringStirring
  4. temperatureheating
  5. customwere continued for a total of 2 hours
  6. temperaturewas cooled
  7. extractionextracted with ether (200, 75 and 75 ml.)
  8. extractionThe combined ether extract
  9. washwas washed several times with 2N-sodium hydroxide
  10. customto remove phenol
  11. dry with materialdried over anhydrous sodium sulphate
  12. customevaporated
  13. distillationThe residue was distilled under water-pump vacuum

Sources & evidence

ORD record
ord-49b009c1c532430fab8405970e7a690f
Source dataset
uspto-grants-1976_10
Patent number
US03987158

Reaction notes

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