Dimethylformamide → 3-Cyanophenoxyacetonitrile

HRID 66769Notes

Reaction equation

HRID 66769 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.Cl[CH2:22][C:23]#[N:24]>O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:22][C:23]#[N:24])#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 133943-Cyanophenol

Product 1

HCID 205290533-Cyanophenoxyacetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The compound 3-cyanophenoxyacetonitrile was prepared by heating 20.0 g of 3-cyanophenol, 30.1 g of anhydrous potassium carbonate and 30 ml of dimethylformamide with stirring in a 250 ml round-bottomed three-necked flask to 70° C. and then 12.7 g of chloroacetonitrile was added dropwise over a 15 minute period with cooling. The temperature of the mixture was held at 70°-80° C. for three hours, after which time the reaction mixture was poured into approximately 700 ml of ice and water which resulted in crystal formation. The crystals were separated by filtering and then washed thoroughly with water. After drying in a vacuum oven, a tan solid 3-cyanophenoxyacetonitrile was obtained.

Workup

  1. customThe compound 3-cyanophenoxyacetonitrile was prepared
  2. temperaturewith cooling
  3. customresulted in crystal formation
  4. customThe crystals were separated
  5. filtrationby filtering
  6. washwashed thoroughly with water
  7. customAfter drying in a vacuum oven

Sources & evidence

ORD record
ord-cb74929a9ac24f9fa00d273291c0ed94
Source dataset
uspto-grants-1982_08
Patent number
US04343808

Reaction notes

Loading…