Nitric Acid → 1-(Benzyloxy)-2-methoxy-4-nitro-5-[(E)-2-nitroethenyl]benzene

HRID 1426991Notes

Reaction equation

[N+:1]([O-])([OH:3])=[O:2].[CH2:5]([O:12][C:13]1[CH:18]=[C:17](/[CH:19]=[CH:20]/[N+:21]([O-:23])=[O:22])[CH:16]=[CH:15][C:14]=1[O:24][CH3:25])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)(=O)C>[CH2:5]([O:12][C:13]1[CH:18]=[C:17](/[CH:19]=[CH:20]/[N+:21]([O-:23])=[O:22])[C:16]([N+:1]([O-:3])=[O:2])=[CH:15][C:14]=1[O:24][CH3:25])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 40 °C

Procedure

69% Nitric acid (10 mL, 155 mmol) was added to a mixture of (E)-2-(benzyloxy)-1-methoxy-4-(2-nitrovinyl)benzene described in Production Example 1-1 (10 g, 35.1 mmol) and acetic acid (70 mL) under nitrogen atmosphere at 25° C., and the mixture was stirred at 40° C. for 3 hours. The reaction mixture was poured onto ice and the precipitate was collected by filteration and then washed with ethanol to obtain the title compound (10.5 g, 91%).

Workup

additionThe reaction mixture was poured onto ice
customthe precipitate was collected by filteration
washwashed with ethanol

Sources & evidence

ORD record: ord-7d855084ce0247d2989aeca1e8e52931
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933099B2

Reaction notes

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