Nitromethane → 2,4-Dimethoxy-1-(2-nitroethenyl)benzene

HRID 978238

Reaction equation

HRID 978238 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[N+:13]([CH3:16])([O-:15])=[O:14].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH:5]=[CH:16][N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 691752,4-DimethoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 2754052,4-Dimethoxy-1-(2-nitroethenyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 100 g of 2,4-dimethoxybenzaldehyde, 102 ml of nitromethane, 46.4 g of ammonium acetate and 500 ml of glacial acetic acid was heated at reflux for 2 hours and quenched in 700 ml of water. The crude precipitate was recrystallized from ethanol to give 105.57 g of 1-(2,4-dimethoxyphenyl)-2-nitroethylene as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customquenched in 700 ml of water
  4. customThe crude precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-2b4d2c70553a4135abe0a89bf28b8897
Source dataset
uspto-grants-1987_05
Patent number
US04663482

Linked notes

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