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Diethyl Malonate → Diethyl 2-(2-nitrobenzylidene)malonate

HRID 2194502
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2194502
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-:3])=[O:2].[C:12]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]([O:20][CH2:21][CH3:22])=[O:19])([O-:3])=[O:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 111012-NitrobenzaldehydeHCID 516892Sodium Bicarbonate

Produkt 1

HCID 231460Diethyl 2-(2-nitrobenzylidene)malonateAusbeute 60,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

32.3 g (0.21 mol) of 2-nitrobenzaldehyde and 35.0 g (0.21 mol) of diethyl malonate were added to 100 mL of acetic anhydride at room temperature. 27.0 g (0.32 mol) of sodium hydrogen carbonate was added to this mixture, and the resulting mixture was allowed to react overnight at 100° C. The reaction mixture was concentrated under reduced pressure to approximately a half of the original volume, and ice water was added to this reaction mixture. The reaction mixture was extracted with ethyl acetate. The organic phase was washed with an aqueous solution of sodium hydrogen carbonate and water in this order, and was dried and concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:9 to 1:4), and thus 37.0 g (yield: 59%) of the title compound was obtained as light yellow crystals.

Aufarbeitung

  1. customto react overnight at 100° C
  2. concentrationThe reaction mixture was concentrated under reduced pressure to approximately a half of the original volume, and ice water
  3. additionwas added to this reaction mixture
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washThe organic phase was washed with an aqueous solution of sodium hydrogen carbonate and water in this order
  6. customwas dried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:9 to 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-f9027566b52444b29a7ce744c83be2e9
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08334236B2

Notizen zur Reaktion

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