2,4-Dichlorophenol → 2-Chloro-4-(2',4'-dichlorophenoxy)benzonitrile

HRID 436982

Reaction equation

HRID 436982 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8](Cl)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[K].[Cl:12][C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[OH:20]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:20][C:14]2[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=2[Cl:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 84492,4-DichlorophenolHCID 810502,4-DichlorobenzonitrileHCID 5462222Potassium

Product 1

HCID 214295702-Chloro-4-(2',4'-dichlorophenoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A stirred solution of 2,4-dichlorobenzonitrile (51.6 g., 0.03 mole) and the potassium salt of 2,4-dichlorophenol (60.3 g., 0.03 mole) in 250 ml. of dimethyl acetamide was heated for 24 hours at 120° C. The cooled reaction mixture was diluted with 1000 ml. of water and the resultant oil was extracted with ether. Evaporation of the ether solution gave 88.0 g. of brown oil. Analysis by v.p.c. showed a 2:1 mixture of the desired compound and the isomeric 4-chloro-2-(2',4'-dichlorophenoxy) benzonitrile. A series of fractional crystallizations from 60°-110° C. petroleum ether gave the desired 2-chloro-4-(2',4'-dichlorophenoxy)benzonitrile with a melting point of 69°-74° C. The minor isomeric by-product melted at 110°-113° C.

Workup

  1. customThe cooled reaction mixture
  2. additionwas diluted with 1000 ml
  3. extractionof water and the resultant oil was extracted with ether
  4. customEvaporation of the ether solution
  5. customgave 88.0 g

Sources & evidence

ORD record
ord-b9edb5826b9c484285f87d566eff734b
Source dataset
uspto-grants-1977_06
Patent number
US04029493

Linked notes

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