Phenol → 4-Phenoxyphthalonitrile

HRID 1886133

Reaction equation

HRID 1886133 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+]([C:11]1[CH:12]=[C:13]([C:19]#[N:20])[C:14](=[CH:17][CH:18]=1)[C:15]#[N:16])([O-])=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:7]([C:11]1[CH:12]=[C:13]([C:19]#[N:20])[C:14](=[CH:17][CH:18]=1)[C:15]#[N:16])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 3718004-Phenoxyphthalonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture was prepared by adding 104 grams (1.1 moles) of phenol, 173 grams (1 mole) of 4-nitrophthalonitrile, and 207 grams of potassium carbonate in 1667 ml of dimethylformamide. The mixture was heated to 70° C. and mechanically stirred. Samples were taken of this reaction mixture periodically and analyzed by GLC. After five hours, the reaction was complete. The 4-phenoxyphthalonitrile was isolated by quenching the crude reaction mixture in ice water. The product was further purified by washing the crude precipitate with dilute sodium carbonate and then water. Finally the 4-phenoxyphthalonitrile was vacuum dried at 60° C.

Workup

  1. customA mixture was prepared

Sources & evidence

ORD record
ord-4f998d14e37b486d88729901f95bc927
Source dataset
uspto-grants-1992_09
Patent number
US05149800

Linked notes

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