Nitromethane → 3,4-Dimethoxy-beta-nitrostyrene

HRID 66456

Reaction equation

HRID 66456 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-eaa97d15e73a41e9ae9ec1504682d09b
Source dataset
uspto-grants-1982_08
Patent number
US04342692

Linked notes

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