Nitromethane → 4-Methoxy-6-(2-nitrovinyl)-1,3-benzodioxole

HRID 496783Notes

Reaction equation

HRID 496783 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH:12]=O)[CH:4]=1.[N+:14]([CH3:17])([O-:16])=[O:15].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=[C:5]([CH:12]=[CH:17][N+:14]([O-:16])=[O:15])[CH:4]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 220161,3-Benzodioxole-5-carboxaldehyde, 7-methoxy-HCID 517165Ammonium Acetate

Product 1

HCID 533971694-Methoxy-6-(2-nitrovinyl)-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

3-Methoxypiperonal (50.0 g) is combined with 71.9 mL of nitromethane in 250 mL of acetic acid; 36 g of ammonium acetate is added, and the mixture is heated to 50° C. for 4 hrs. Solvents are removed in vacuo; the residue is taken up in water and stirred for 20 min. The solution is filtered; the filtrate is washed with water, then ether, to give 51.8 g of a yellow solid.

Workup

  1. customSolvents are removed in vacuo
  2. filtrationThe solution is filtered
  3. washthe filtrate is washed with water

Sources & evidence

ORD record
ord-7f6fdaa25a814284887ef8d00a37d2ab
Source dataset
uspto-grants-2005_09
Patent number
US06946481B1

Reaction notes

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