Acrylonitrile → HCID 20379424, compound

HRID 2051652Notes

Reaction equation

HRID 2051652 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](#[N:18])[CH:16]=[CH2:17].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>CO.O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:17][CH2:16][C:15]#[N:18])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 132544-PhenoxyphenolHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 20379424HCID 20379424, compoundYield 34.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-(p-Phenoxyphenoxy)propionitrile was prepared by heating under reflux for 18 hours a mixture of 25 g of p-phenoxyphenol, 28.4 g of acrylonitrile and 5 ml of a 40% solution of benzyltrimethylammonium hydroxide in methanol. It was worked up by cooling, diluting with 400 ml water, extracting using ethyl acetate; washing the organic layer with 5% aqueous sodium hydroxide, drying, evaporating the solvent, and recrystallizing from hexane to yield 11.1 g of 3-(p-phenoxyphenoxy)propionitrile m.p. 81-3° C.

Workup

  1. custom3-(p-Phenoxyphenoxy)propionitrile was prepared
  2. temperatureby heating
  3. temperatureunder reflux for 18 hours
  4. temperatureby cooling
  5. extractionextracting
  6. washwashing the organic layer with 5% aqueous sodium hydroxide
  7. customdrying
  8. customevaporating the solvent
  9. customrecrystallizing from hexane

Sources & evidence

ORD record
ord-201d73a9c1fd4f81a2917a38dc74b80e
Source dataset
uspto-grants-1980_01
Patent number
US04181729

Reaction notes

Loading…