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

HRID 30077

Reaction equation

HRID 30077 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.C([O-])(=O)C.[NH4+].[N+:18]([CH3:21])([O-:20])=[O:19]>C(O)(=O)C>[CH3:12][O:11][C:10]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:21]/[N+:18]([O-:20])=[O:19])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8419VeratraldehydeHCID 517165Ammonium Acetate

Product 1

HCID 7096881,2-Dimethoxy-4-(2-nitrovinyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

207.0 g of 3,4-dimethoxybenzaldehyde, 100.0 g of ammonium acetate and 125 ml of nitromethane are heated to boiling for 3-4 h in 1.0 l of glacial acetic acid. After cooling in an ice bath, the precipitate is filtered off with suction, rinsed with glacial acetic acid and petroleum ether and dried. M.p.: 140-141° C. Yield: 179.0 g.

Workup

  1. temperatureAfter cooling in an ice bath
  2. filtrationthe precipitate is filtered off with suction
  3. washrinsed with glacial acetic acid and petroleum ether
  4. customdried

Sources & evidence

ORD record
ord-6ba2f0ae594741aca514a216ec8fd8e2
Source dataset
uspto-grants-2008_09
Patent number
US07423046B2

Linked notes

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