Benzene → Ethyl 5,5-diphenylpenta-2,4-dienoate

HRID 1007759

Reaktionsgleichung

Reaktionsgleichung von HRID 1007759
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([CH:22]=C1CCP(C2C=CC=CC=2)C1(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH2:20][CH3:21])=[O:18].C(O)(=O)C1C=CC=CC=1.C1C=CC=CC=1>CCCCCC>[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=[CH:22][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 241BenzeneHCID 243Benzoic AcidHCID 710273,3-DiphenylacroleinHCID 68574662HCID 68574662, Verbindung

Produkt 1

HCID 53936700Ethyl 5,5-diphenylpenta-2,4-dienoateAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

β-Phenylcinnamaldehyde (3.36 g), (carbethoxymethylene)triphenylphospholane (5.68 g), and benzoic acid (0.2 g) were added to anhydrous benzene (80 mL), and the mixture was refluxed under stirring for 3.5 hours. Subsequently, the resultant mixture was cooled to room temperature and condensed under reduced pressure. n-Hexane was added to the residue, and the insoluble matter was collected through filtration and washed several times with n-hexane. The filtrate and the resulting wash liquid were combined and condensed under reduced pressure. The product was purified through silica gel column chromatography (silica gel 40 g, eluent; n-hexane:ethyl acetate=50:1), to thereby yield 3.70 g of the product of interest (yield 82.4%).

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. customcondensed under reduced pressure
  3. filtrationthe insoluble matter was collected through filtration
  4. washwashed several times with n-hexane
  5. washThe filtrate and the resulting wash liquid
  6. customcondensed under reduced pressure
  7. customThe product was purified through silica gel column chromatography (silica gel 40 g, eluent; n-hexane:ethyl acetate=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-5e062507c5c34e06be7b61cd6e4e2387
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06797711B2

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