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

HRID 1427030Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[N+:27]([CH3:30])([O-:29])=[O:28]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[CH:30]/[N+:27]([O-:29])=[O:28])[CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

3-(Benzyloxy)-4-(2-methoxyethoxy)benzaldehyde described in Production Example 20-2 (17.6 g, 61.5 mmol) was dissolved in acetic acid (49.3 mL), then ammonium acetate (5.69 g, 73.8 mmol) and nitromethane (8.32 mL, 154 mmol) were added under nitrogen atmosphere at room temperature, and the mixture was heated under reflux at 130° C. for 2 hours. The mixture was cooled to room temperature and then the precipitate was collected by filteration and washed with ethanol to quantitatively obtain the title compound.

Workup

temperaturethe mixture was heated
temperatureThe mixture was cooled to room temperature
customthe precipitate was collected by filteration
washwashed with ethanol

Sources & evidence

ORD record: ord-b43a95b6bbde413d878e934d654a5d39
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933099B2

Reaction notes

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