Nitrogen → 1-Methoxy-2-nitro-3-(2-nitroprop-1-en-1-yl)benzene

HRID 480572Notes

Reaction equation

HRID 480572 reaction equation
N#N.[N+:3]([C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:14](O)[CH:15]([N+:17]([O-:19])=[O:18])[CH3:16])([O-:5])=[O:4].C(OC(=O)C)(=O)C.C1OCCOCCOCCOCCOCCOC1.[F-].[K+]>O>[N+:3]([C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:14]=[C:15]([N+:17]([O-:19])=[O:18])[CH3:16])([O-:5])=[O:4]

Participants

7

Reactant 5

HCID 947NitrogenHCID 7918Acetic AnhydrideHCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 11299824HCID 11299824, compound

Product 1

HCID 534141941-Methoxy-2-nitro-3-(2-nitroprop-1-en-1-yl)benzeneYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 5 L three-necked round-bottomed flask equipped with a mechanical stirrer and a N2 bubbler were added 1-(2-nitro-3-methoxyphenyl)-2-nitropropanol (170 g, 0.66 mol), acetic anhydride (450 mL), 18-Crown-6 (17 g) and KF (38.25 g). The reaction mixture was stirred at RT for 64 h, then cooled in an ice-water bath. Water (2250 mL) was added slowly. The resulting slurry was stirred at 0° C. for 2 h and then filtered. The cake was washed with DI water (3×250 mL) and suction dried for 20 h to give 1-(2-nitro-3-methoxyphenyl)-2-nitropropene (150.7 g, 96% yield). 1H NMR (CDCl3) δ2.30 (s, 3H), 3.95 (s, 3H), 6.94 (d, J=7.8 Hz, 1H), 7.13 (d, J=8.5 Hz, 1H), 7.53 (pseudo t, J=8.1 Hz, 1H), 7.89 (s, 1H).

Workup

  1. customTo a 5 L three-necked round-bottomed flask equipped with a mechanical stirrer
  2. temperaturecooled in an ice-water bath
  3. stirringThe resulting slurry was stirred at 0° C. for 2 h
  4. filtrationfiltered
  5. washThe cake was washed with DI water (3×250 mL) and suction
  6. customdried for 20 h

Sources & evidence

ORD record
ord-2ab6a44b0c3e4d939979f1f42f2be270
Source dataset
uspto-grants-2003_11
Patent number
US06653304B2

Reaction notes

Loading…