Water → HCID 18956674, compound

HRID 2226195Notes

Reaction equation

HRID 2226195 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:16].Cl[CH2:18][C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:16][CH2:18][C:19]#[N:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 19034580HCID 19034580, compound

Product 1

HCID 18956674HCID 18956674, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 14.99 g of 2-chloro-4-(3-chlorophenoxy)phenol, 4.44 g of chloroacetonitrile and 8.94 g of potassium carbonate in 150 ml of dimethylformamide was stirred at a temperature of 70° to 80° C. in an oil bath for 5 hours. The reaction mixture was cooled to room temperature, poured into water and extracted twice with 100 ml of ethyl acetate. The extracts were combined together, washed twice with 200 ml of water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 14.0 g of [2-chloro-4-(3-chlorophenoxy)phenoxy]acetonitrile as a crude product.

Workup

  1. extractionextracted twice with 100 ml of ethyl acetate
  2. washwashed twice with 200 ml of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e1f93b3f79240a988a06ce005f75bb9
Source dataset
uspto-grants-1994_09
Patent number
US05346920

Reaction notes

Loading…