Nitromethane → 1,2,3-Trimethoxy-5-((E)-2-nitrovinyl)benzene

HRID 428126

Reaction equation

HRID 428126 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[N+:15]([CH3:18])([O-:17])=[O:16].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])/[CH:6]=[CH:18]/[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 68583,4,5-TrimethoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 53549161,2,3-Trimethoxy-5-((E)-2-nitrovinyl)benzeneYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3,4,5-trimethoxybenzaldehyde (9.80 g, 50 mmol), nitromethane (18 ml), ammonium acetate (4.11 g) and acetic acid (38 ml) was heated and refluxed for 2 hours. After the reaction mixture was concentrated under reduced pressure, 10% aqueous sodium hydroxide solution was added to the residue and the reaction mixture was extracted with dichloromethane, washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure and the residue was purified by silica gel chromatography (dichloromethane) and recrystallized to yield trans-3,4,5-trimethoxy-β-nitrostyrene (4.96 g, 41%). Properties: mp 116-118° C. (ethanol)

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 2 hours
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure, 10% aqueous sodium hydroxide solution
  4. additionwas added to the residue
  5. extractionthe reaction mixture was extracted with dichloromethane
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled out under reduced pressure
  9. customthe residue was purified by silica gel chromatography (dichloromethane)
  10. customrecrystallized

Sources & evidence

ORD record
ord-10f4f322073948839ee1d7fbdcce32e8
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Linked notes

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