Nitromethane → 1-Chloro-3-(2-nitroethenyl)benzene
Reaction equation
[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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- temperaturewas heated
- temperatureat reflux temperature for 3 h
- additionpoured onto ice
- filtrationThe precipitate was filtered
- customcrystallized from ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-8a9dfc9e6b4442e382afa28c9f122cb5
- Source dataset
- uspto-grants-1993_09
- Patent number
- US05248677
Reaction notes
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