Water → HCID 23337331, compound

HRID 902997Notes

Reaction equation

HRID 902997 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[O-:13].[K+].Cl[C:16]1[CH:21]=[C:20](Cl)[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].[OH2:26]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:11])([F:12])[F:10])[CH:5]=[CH:4][C:3]=1[O:13][C:16]1[CH:21]=[C:20]([O:26][C:3]2[CH:4]=[CH:5][C:6]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:7][C:2]=2[Cl:1])[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 118992,4-DichloronitrobenzeneHCID 23713194HCID 23713194, compound

Product 1

HCID 23337331HCID 23337331, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.1 g of metallic sodium in 8 ml of methanol was added to a solution of 1.2 g (0.002 mole) of 2,4-bis(2-chloro-4-trifluoromethoxy-phenoxy)nitrobenzene in benzene. The mixture was heated with stirring at 40°-50° C. in a water bath for 1.5 hours. The reaction mixture was thoroughly washed with a dilute aqueous sodium hydroxide solution and then with water, dehydrated over anhydrous sodium sulfate, and freed from the benzene by distillation to obtain a crude product. The crude product was purified by chromatography on silica gel to obtain 0.7 g of the intended product (nD20 1.5562; 84% yield). 2,4-Bis(2-chloro-4-trifluoromethoxyphenoxy)-nitrobenzene was synthesized in the following way: 11.0 Grams (0.044 mole) of potassium 2-chloro-4-trifluoromethoxyphenolate and 3.2 g (0.017 mole) of 2,4-dichloronitrobenzene were heated under reflux in 100 ml of dimethylformamide for one hour. After cooling, the reaction mixture was poured into about 500 ml of water and then extracted with benzene. The benzene layer was thoroughly washed successively with dilute aqueous sodium hydroxide solution, dilute hydrochloric acid and water, then dehydrated, and concentrated. The resulting oily substance was distilled under reduced pressure to obtain 5.3 g (57% yield) of the intended product boiling at 170°-185° C./0.1 mmHg.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with benzene
  3. washThe benzene layer was thoroughly washed successively with dilute aqueous sodium hydroxide solution, dilute hydrochloric acid and water
  4. concentrationconcentrated
  5. distillationThe resulting oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-41690e63ceea4f238e29679fefd52809
Source dataset
uspto-grants-1980_10
Patent number
US04226616

Reaction notes

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