Nitrogen → 2-Chloro-4-methoxy-1-nitrobenzene

HRID 1089816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089816
N#N.[H-].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]([OH:15])[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13].[CH3:16]OS(OC)(=O)=O.[NH4+].[OH-]>>[Cl:5][C:6]1[CH:7]=[C:8]([O:15][CH3:16])[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]

Komponenten

6

Edukt 5

HCID 947NitrogenHCID 6497Dimethyl SulfateHCID 102833-Chloro-4-nitrophenolHCID 14923Ammonium HydroxideHCID 24758Sodium hydride

Produkt 1

HCID 5937892-Chloro-4-methoxy-1-nitrobenzeneAusbeute 72,4 %

Versuchsvorschrift

In an atomosphere of N2 were added to a stirred suspension of 31 g NaH in 2.2 l anhydrous THF 199.5 g (1.15 mole) 3-chloro-4-nitrophenol (3). This was followed by the addition of dimethylsulfate (575 ml). The whole mixture was heated under reflux during 1.5 h. After cooling, it was poured into a cold (0° C.) diluted NH4OH solution, to destroy the excess of dimethylsulfate, and stirred for two hours. The product was isolated by extraction with diethylether. The ethereal extracts were dried with MgSO4 and evaporated at reduced pressure affording 156 g (72.4%) of 3-chloro-4-nitroanisole.

Aufarbeitung

  1. temperatureThe whole mixture was heated
  2. temperatureunder reflux during 1.5 h
  3. temperatureAfter cooling
  4. customto destroy the excess of dimethylsulfate
  5. customThe product was isolated by extraction with diethylether
  6. dry with materialThe ethereal extracts were dried with MgSO4
  7. customevaporated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9c079650b12644a199ff07f60105eabf
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05079257

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