Nitromethane → TRANS-3-BENZYLOXY-4-METHOXY-BETA-NITROSTYRENE

HRID 1426990Notes

Reaction equation

HRID 1426990 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[N+:24]([CH3:27])([O-:26])=[O:25]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:27]/[N+:24]([O-:26])=[O:25])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 688198TRANS-3-BENZYLOXY-4-METHOXY-BETA-NITROSTYRENEYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

Commercially available 3-benzyloxy-4-methoxybenzaldehyde (30 g, 124 mmol) was dissolved in acetic acid (100 mL), then ammonium acetate (10.8 g, 140 mmol) and nitromethane (16.8 mL, 310 mmol) were added under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 130° C. for 2 hours and 20 minutes. The mixture was cooled to room temperature, then the precipitate was collected by filteration and washed with ethanol to obtain the title compound (28.5 g, 81%).

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-05fdb24916634a0f91f7dd78d069f8e7
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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