Nitromethane → (E)-2-(Benzyloxy)-1-ethoxy-4-(2-nitrovinyl)benzene

HRID 1427013Notes

Reaction equation

HRID 1427013 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH3:19])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[N+:25]([CH3:28])([O-:27])=[O:26]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:28]/[N+:25]([O-:27])=[O:26])[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 8185733-(Benzyloxy)-4-ethoxybenzaldehyde

Product 1

HCID 86730317(E)-2-(Benzyloxy)-1-ethoxy-4-(2-nitrovinyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

3-(Benzyloxy)-4-ethoxy benzaldehyde described in Production Example 15-2 (14.5 g, 56.4 mmol) was dissolved in acetic acid (45 mL), then ammonium acetate (5.22 g, 67.7 mmol) and nitromethane (7.5 mL, 138 mmol) were added under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 130° C. for 2.5 hours. The mixture was cooled to room temperature and the precipitate was collected by filteration and washed with ethanol to quantitatively obtain the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. customthe precipitate was collected by filteration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-14da2fb00edb4a4eb7b54a86918448d5
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

Loading…