Acetic Anhydride → Diethyl [(2,4-dinitrophenyl)methylidene]propanedioate

HRID 2269745Notes

Reaction equation

HRID 2269745 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[CH2:15](C(CC)(C([O-])=O)C([O-])=O)[CH3:16].[C:26](=[O:29])([O-:28])O.[K+].[C:31]([O:34][C:35](=[O:37])[CH3:36])(=O)[CH3:32]>O>[N+:1]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1[CH:6]=[C:36]([C:35]([O:34][CH2:31][CH3:32])=[O:37])[C:26]([O:28][CH2:15][CH3:16])=[O:29])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 682502,4-DinitrobenzaldehydeHCID 516893Potassium BicarbonateHCID 69515632,2-Diethylpropanedioate

Product 1

HCID 13142394Diethyl [(2,4-dinitrophenyl)methylidene]propanedioate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of 2,4-dinitrobenzaldehyde (25 g), diethylmalonate (20.3 g), potassium hydrogencarbonate (19.1 g), and acetic anhydride (50 ml) was stirred at 110° C. under nitrogen atmosphere for one hour. The reaction mixture was cooled, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution and then dried and concentrated. The residue was purified by alumina column chromatography (eluent: hexane/ethyl acetate=4: 1) to obtain the entitled compound (24 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution and then dried
  5. concentrationconcentrated
  6. customThe residue was purified by alumina column chromatography (eluent: hexane/ethyl acetate=4: 1)

Sources & evidence

ORD record
ord-43331de60e3a459a9a496ddce1b9805f
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

Loading…