Acetic Acid → 3,4-Dimethoxy-beta-nitrostyrene

HRID 849712Notes

Reaction equation

HRID 849712 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.C([O-])(=O)C.[NH4+].[N+:22]([CH3:25])([O-:24])=[O:23]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:25][N+:22]([O-:24])=[O:23])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 8419VeratraldehydeHCID 517165Ammonium Acetate

Product 1

HCID 2220933,4-Dimethoxy-beta-nitrostyreneYield 53.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 250 mL flask was placed 42.45 g of 3,4-dimethoxybenzaldehyde (0.255 mole, 1 eq.), 64 mL of glacial acetic acid (4.0 M), 9.83 g of ammonium acetate (0.128 mole, 0.5 eq), and 15.2 mL of nitromethane (0.281 mole, 1.1 eq.). The mixture was stirred well and heated to reflux for 1.5 hour and allowed to cool to room temperature. The reaction mass solidified and was dissolved in methylene chloride (500 mL) and washed with water (2×400 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated on a rotary evaporator to provide 56.33 g of crude product. Crystallization of the product from ethanol (240 mL) and acetone (100 mL) provided 28.66 g of 2-(3,4-dimethoxypheny)-nitroethene (0.137 mole), 53.7% yield.

Workup

  1. customIn a 250 mL flask was placed
  2. temperatureheated
  3. temperatureto reflux for 1.5 hour
  4. washwashed with water (2×400 mL)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customto provide 56.33 g of crude product
  9. customCrystallization of the product from ethanol (240 mL) and acetone (100 mL)

Sources & evidence

ORD record
ord-68241b5dc12148f5a7b27f1a54bd06db
Source dataset
uspto-grants-2000_01
Patent number
US06013841

Reaction notes

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