4-Cyanophenol → 4-((5-Chloropentyl)oxy)benzonitrile

HRID 6068

Reaktionsgleichung

Reaktionsgleichung von HRID 6068
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].[H][H].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][Cl:20]>CN(C)C=O>[Cl:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Komponenten

6

Edukt 4

HCID 130194-CyanophenolHCID 24758Sodium hydrideHCID 960701-Bromo-5-chloropentaneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 193815104-((5-Chloropentyl)oxy)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 16.9 g (135 mmol) p-cyanophenol in 169 mL of dimethylformamide (DMF), cooled in an ice-bath is added in portions 6.5 g (135 mmol) sodium hydride (50% dispersion in oil). The reaction is stirred and allowed to warm-up to room temperature until no further hydrogen evolution is observed. The solution is then cooled in an ice-bath and a solution of 1-bromo-5-chloro-pentane 25 g (135 mmol) in 84 mL of dimethylformamide is added. The reaction is allowed to warm up to room temperature and stirred for 18 h. The reaction is then poured onto water and the resulting solid filtered off and dried to give 4-(5-chloropentoxy) benzonitrile, m.p. 52°-54° C.

Aufarbeitung

  1. temperatureThe solution is then cooled in an ice-bath
  2. stirringstirred for 18 h
  3. additionThe reaction is then poured onto water
  4. filtrationthe resulting solid filtered off
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-47bbd098cb2a4725a243aeb6e8e75282
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246965

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