Nitric Acid → (E)-1-(Benzyloxy)-2-(2-ethoxyethoxy)-4-nitro-5-(2-nitrovinyl)benzene

HRID 1427037Notes

Reaction equation

HRID 1427037 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][CH2:25][CH2:26][O:27][CH2:28][CH3:29])[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][CH2:25][CH2:26][O:27][CH2:28][CH3:29])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 86730339(E)-2-(Benzyloxy)-1-(2-ethoxyethoxy)-4-(2-nitrovinyl)benzene

Product 1

HCID 86730340(E)-1-(Benzyloxy)-2-(2-ethoxyethoxy)-4-nitro-5-(2-nitrovinyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

69% Nitric acid (11 mL, 171 mmol) was added to a solution of (E)-2-(benzyloxy)-1-(2-ethoxyethoxy)-4-(2-nitrovinyl)benzene described in Production Example 24-3 (15.4 g, 44.9 mmol) and acetic acid (100 mL) at 25° C., and the mixture was stirred for 6 hours. The reaction liquid was poured onto ice. The suspension was subjected to suction filtration and the product was washed with water to quantitatively obtain the title compound.

Workup

  1. customThe reaction liquid
  2. additionwas poured onto ice
  3. filtrationThe suspension was subjected to suction filtration
  4. washthe product was washed with water

Sources & evidence

ORD record
ord-29fa41c3779048c080f754436f6facb3
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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