Nitromethane → 1-Chloro-3-(2-nitroethenyl)benzene

HRID 6393

Reaktionsgleichung

Reaktionsgleichung von HRID 6393
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C([O-])(=O)C.[NH4+].[N+:15]([CH3:18])([O-:17])=[O:16].[OH-].[K+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:18][N+:15]([O-:17])=[O:16])[CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 6375NitromethaneHCID 114773-ChlorobenzaldehydeHCID 14797Potassium HydroxideHCID 517165Ammonium Acetate

Produkt 1

HCID 27316461-Chloro-3-(2-nitroethenyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 28.11 g (200 mmol) of 3-chlorobenzaldehyde, 15.4 g of ammonium acetate and 32.5 mL of nitromethane in 230 mL of glacial acetic acid was heated at reflux temperature for 3 h and then poured onto ice. The resultant aqueous mixture was made basic by the addition of 45% aqueous potassium hydroxide. The precipitate was filtered and crystallized from ethyl acetate/hexane to give 5 g of the title compound. The filtrate was concentrated to afford an additional 13.5 g of product.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux temperature for 3 h
  3. additionpoured onto ice
  4. filtrationThe precipitate was filtered
  5. customcrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8a9dfc9e6b4442e382afa28c9f122cb5
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248677

Verknüpfte Notizen

Wird geladen…