Acetic Acid → Methyl 5-(2-nitrophenyl)-3-oxopent-4-enoate

HRID 2351942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2351942
[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:18][CH3:19])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].N1CCCCC1.C(O)(=O)C>C1C=CC=CC=1>[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[CH:16][C:14](=[O:15])[CH2:13][C:12]([O:18][CH3:19])=[O:17])([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 8082PiperidineHCID 111012-Nitrobenzaldehyde

Produkt 1

HCID 53723829Methyl 5-(2-nitrophenyl)-3-oxopent-4-enoateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

o-Nitrobenzaldehyde (7.6 g, 0.05 mole) and methyl acetoacetate (5.8 g, 0.05 mole) are dissolved in benzene (40 ml), and thereto are added piperidine (0.2 ml) and acetic acid (0.6 ml), and the mixture is refluxed for 5 hours. The produced water is removed, and when a stoichiometic amount of water is distilled off, the reaction is stopped. After completion of the reaction, the reaction mixture is washed with 5% hydrochloric acid and then with water, and the solvent is distilled off under reduced pressure to give the title compound (12.2 g, yield 98%) as a brown oil.

Aufarbeitung

  1. temperaturethe mixture is refluxed for 5 hours
  2. customThe produced water is removed
  3. distillationwhen a stoichiometic amount of water is distilled off
  4. customAfter completion of the reaction
  5. washthe reaction mixture is washed with 5% hydrochloric acid
  6. distillationwith water, and the solvent is distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b57d384df9ce43ceb72c67800f3f58dd
Quelldatensatz
uspto-grants-1989_10
Patentnummer
US04874773

Notizen zur Reaktion

Wird geladen…