Acrylonitrile → 3-(4-Methoxyphenoxy)propanenitrile

HRID 428176Notes

Reaction equation

HRID 428176 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[C:10](#[N:13])[CH:11]=[CH2:12]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:12][CH2:11][C:10]#[N:13])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 90154-Methoxyphenol

Product 1

HCID 1142473-(4-Methoxyphenoxy)propanenitrile

Procedure

A mixture of 4-methoxyphenol (10 g:80.5 mmol) and Triton B (2.29 ml:14.5 mmol 0. 18 eq.) in acrylonitrile (50 ml) is heated at reflux for 48 hours. After the solvent has been partially removed, the products are extracted with ethyl acetate and washed with water and then with a 6N hydrochloric acid solution. The residual chestnut-brown oil is purified on a flash silica column eluted with an AcOEt/PE gradient.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 48 hours
  3. customAfter the solvent has been partially removed
  4. extractionthe products are extracted with ethyl acetate
  5. washwashed with water
  6. customThe residual chestnut-brown oil is purified on a flash silica column
  7. washeluted with an AcOEt/PE gradient

Sources & evidence

ORD record
ord-30a09853878a43d3afd334255626989d
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

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