Potassium Carbonate → 2-Phenyl-2-(2-cyanomethoxyphenoxy)acetonitrile

HRID 267792

Reaction equation

HRID 267792 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[O:4][CH2:5][C:6]#[N:7].Cl[CH:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:14]#[N:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:16]1([CH:13]([O:1][C:2]2[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=2[O:4][CH2:5][C:6]#[N:7])[C:14]#[N:15])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 123763172-Chloro-2-phenylacetonitrile2×HCID 215539352-(2-Hydroxyphenoxy)acetonitrile

Product 1

HCID 215539672-Phenyl-2-(2-cyanomethoxyphenoxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(2-hydroxyphenoxy)acetonitrile (14.9 g., 0.1 mole), 2-chloro-2-phenylacetonitrile (15.2 g., 0.1 mole), finely powdered potassium carbonate (13.8 g., 0.1 mole) and 80 ml. of acetone is refluxed 3 hours. The mixture is then treated with 2-chloro-2-phenylacetonitrile (7.6 g., 0.05 mole) and potassium carbonate (6.9 g., 0.5 mole) and refluxed six hours. The mixture is filtered, the solids washed with acetone and the combined filtrate evaporated in vacuo to give an oil. Crystallization of the oil affords 2-phenyl-2-(2-cyanomethoxyphenoxy)acetonitrile.

Workup

  1. temperaturerefluxed six hours
  2. filtrationThe mixture is filtered
  3. washthe solids washed with acetone
  4. customthe combined filtrate evaporated in vacuo
  5. customto give an oil
  6. customCrystallization of the oil

Sources & evidence

ORD record
ord-fb7af966e19f41d4a3a52ead66b7bcdc
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Linked notes

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