Nitromethane → Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-

HRID 256190Notes

Reaction equation

HRID 256190 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]([CH2:6][CH2:21][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 10036050Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-

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-cd89cbff125d46a8ad67f6dbbb6088d3
Source dataset
uspto-grants-1987_10
Patent number
US04701461

Reaction notes

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