Water → Benzonitrile, 2-(2,4-dichlorophenoxy)-5-nitro-

HRID 1155732

Reaktionsgleichung

Reaktionsgleichung von HRID 1155732
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[OH-].[Na+].Cl[C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 84492,4-DichlorophenolHCID 14798Sodium HydroxideHCID 855042-Chloro-5-nitrobenzonitrile

Produkt 1

HCID 514833Benzonitrile, 2-(2,4-dichlorophenoxy)-5-nitro-Ausbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5.0 g (0.0307 moles) of 2,4-dichlorophenol dissolved in 150 ml of DMSO was added 1.23 g (0.0307 moles) of NaOH. The slurry was heated at 60° C. for 15 minutes and 5.04 g (0.0276 moles) of 2-chloro-5-nitrobenzonitrile was added. The mixture was heated at 75° C. for 3.25 hrs. The reaction mixture was cooled and poured into water. The product was collected by filtration, washed well with water and dried, yielding 8.1 g of product (95.3% yield). Recrystallization from ethanol afforded purified 2-(2,4-dichlorophenoxy)-5-nitrobenzonitrile, mp 153.5°-154.5° C.

Aufarbeitung

  1. temperatureThe mixture was heated at 75° C. for 3.25 hrs
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe product was collected by filtration
  4. washwashed well with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ebd384e1d9024f15ba073ecbf74b42c4
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04332820

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