Nitromethane → HCID 54204816, compound

HRID 654390Notes

Reaction equation

HRID 654390 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:14]([O-:16])=[O:15])=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=O.C([O-])(=O)C.[NH4+].[N+:22]([CH3:25])([O-:24])=[O:23]>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3]1[C:4]([N+:14]([O-:16])=[O:15])=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])[CH:6]=[CH:25][N+:22]([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 18962544HCID 18962544, compound

Product 1

HCID 54204816HCID 54204816, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of 20 g (0.088 mole) of 3,5-dimethoxy-4-hydroxy-2-nitrobenzaldehyde and 21 g (0.27 mole) of dry ammonium acetate in 400 cm3 of acetic anhydride and 15.8 g (0.26 mole) of nitromethane is heated under reflux for 2 hours. The reaction mixture is cooled, then the precipitate is filtered off. After washing with water, recrystallization from an ethanol-water mixture and drying under vacuum, 13.9 g of the desired product is obtained in the form of orangish-yellow crystals (yield=58%).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe precipitate is filtered off
  5. washAfter washing with water, recrystallization from an ethanol-water mixture
  6. customdrying under vacuum

Sources & evidence

ORD record
ord-63a377f4ad3f4a4bbc1e011cc403d557
Source dataset
uspto-grants-1992_07
Patent number
US05131911

Reaction notes

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