Nitromethane → 3,4-Dimethoxy-beta-nitrostyrene

HRID 1249507Notes

Reaction equation

HRID 1249507 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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:21][N+:18]([O-:20])=[O:19])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 8419VeratraldehydeHCID 517165Ammonium Acetate

Product 1

HCID 2220933,4-Dimethoxy-beta-nitrostyrene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 1 l. r.b. flask 100 g. (0.6 mole) of 3,4-dimethoxybenzaldehyde, 40 g. (0.52 mole) of ammonium acetate, 50 ml. (0.93 mole) of nitromethane, and 400 ml. of glacial acetic acid were combined and refluxed for 2 hours. The solution was then cooled to room temperature overnight. Yellow crystals were then collected via suction filtration and washed with hexane and ether. 73 g. of desired product were collected with m.p. 133°-134° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationYellow crystals were then collected via suction filtration
  3. washwashed with hexane and ether
  4. customof desired product were collected with m.p. 133°-134° C.

Sources & evidence

ORD record
ord-ad79d68fe39a41faa3aff1e310376ae4
Source dataset
uspto-grants-1986_12
Patent number
US04632929

Reaction notes

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