Réaction #6489

Équation de réaction

potassium hydroxide

3-chlorobenzaldehyde

ammonium acetate

nitromethane

→

title compound

2-(3-Chlorophenyl)-1-nitroethene

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   Températureat reflux temperature for 3 h
3. 3
   workup.ADDITIONpoured onto ice
4. 4
   FiltrationThe precipitate was filtered
5. 5
   Autrecrystallized from ethyl acetate/hexane

Mode opératoire

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.

Source