Nitroethane → 1-Nitro-2-(2-nitroprop-1-en-1-yl)benzene

HRID 1423358Notes

Reaction equation

HRID 1423358 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].C([O-])(=O)C.[NH4+].[N+:17]([CH2:20][CH3:21])([O-:19])=[O:18]>CC(O)=O.CCOC(C)=O>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[C:20]([N+:17]([O-:19])=[O:18])[CH3:21])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6587NitroethaneHCID 111012-NitrobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 27313161-Nitro-2-(2-nitroprop-1-en-1-yl)benzene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-nitrobenzaldehyde (5.0 g, 33.1 mmol) and ammonium acetate (2.55 g, 33.1 mmol) in AcOH (20 mL) was treated dropwise at 20° C. with nitroethane (2.84 mL, 39.7 mmol). The resulting solution was heated under reflux for 2 h, then cooled and diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3 solution and brine, then dried over Na2SO4. Filtration and removal of the volatiles gave a residue that was purified on silica gel (gradient elution, 0-40% EtOAc/hexanes) to give the title compound as an oil. (2.3 g, 33%). LCMS (ES+) m/z 209 (M+H)+

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 2 h
  3. temperaturecooled
  4. washThe organic layer was washed with saturated aqueous NaHCO3 solution and brine
  5. dry with materialdried over Na2SO4
  6. filtrationFiltration and removal of the volatiles
  7. customgave a residue that
  8. customwas purified on silica gel (gradient elution, 0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b42400b64d574091ad497799822f2ea2
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

Loading…