Nitric Acid → 1-Nitro-2-[(1E)-2-nitroethenyl]-4,5-bis(phenylmethoxy)benzene

HRID 1982216Notes

Reaction equation

HRID 1982216 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:12]=[CH:13][N+:14]([O-:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:28]([O-])([OH:30])=[O:29]>CC(O)=O>[CH2:21]([O:20][C:19]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][C:11](/[CH:12]=[CH:13]/[N+:14]([O-:16])=[O:15])=[C:17]([N+:28]([O-:30])=[O:29])[CH:18]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 5637763,4-Dibenzyloxy-beta-nitrostyrene

Product 1

HCID 131570911-Nitro-2-[(1E)-2-nitroethenyl]-4,5-bis(phenylmethoxy)benzeneYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

3,4-Dibenzyloxy -β-nitrostyrene (12) (67.2 g; 0.186 mol) is dispersed in 1.5 L CH3CO2H. HNO3 (d 1.42) is added until the temperature reaches 40° C. The mixture is cooled to 20° C., and the remainder of the 375 mL HNO3 is added without further cooling. After stirring at 23° C. for three hours, the reaction mixture is poured onto 2 kg of ice, and filtered. The yellow powder is washed well with H2O. Recrystallization from CH3CO2H affords 70.3 g (93%) of (13) as yellow needles; mp 162°-164° C.

Workup

  1. customreaches 40° C
  2. filtrationfiltered
  3. washThe yellow powder is washed well with H2O
  4. customRecrystallization from CH3CO2H

Sources & evidence

ORD record
ord-d92e7cb8821f49ca82464deaaaee494a
Source dataset
uspto-grants-1986_06
Patent number
US04595765

Reaction notes

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