Nitroethane → 1,2-Dimethoxy-4-(2-nitroprop-1-enyl)benzene

HRID 1363479Notes

Reaction equation

HRID 1363479 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]([CH2:21][CH3:22])([O-:20])=[O:19]>>[CH3:12][O:11][C:10]1[CH:9]=[CH:8][C:5]([CH:6]=[C:21]([N+:18]([O-:20])=[O:19])[CH3:22])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 8419VeratraldehydeHCID 517165Ammonium Acetate

Product 1

HCID 954741,2-Dimethoxy-4-(2-nitroprop-1-enyl)benzeneYield 50%

Conditions

Temperature
105 °C

Procedure

4.99 g (30.0 mmol) 3,4-dimethoxybenzaldehyde (Aldrich, Milwaukee, Wis.), 15.0 g (194 mmol) ammonium acetate (Fluka), and 70 g (930 Mmol) nitroethane, 98% (Aldrich) were combined in a 100 ml round bottom flask equipped with magnetic stirrer and nitrogen inlet. The reaction mixture was heated to 105° C. for 90 minutes and the solvent was removed under vacuum to give a dark yellow liquid which was recrystallized from cold methyl alcohol three times to give yellow-orange needles in 50% yield. 1H NMR spectra is shown in FIG. 3.

Workup

  1. customequipped with magnetic stirrer and nitrogen inlet
  2. customthe solvent was removed under vacuum
  3. customto give a dark yellow liquid which
  4. customwas recrystallized from cold methyl alcohol three times
  5. customto give yellow-orange needles in 50% yield

Sources & evidence

ORD record
ord-4e93ae23720241b3a8723d264eb37e29
Source dataset
uspto-grants-2011_02
Patent number
US07884228B1

Reaction notes

Loading…