Vanillin → 1-(4'-Hydroxy,3'-methoxyphenyl)-4-phenoxy-1-butene-3-one

HRID 1646110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1646110
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH3:11].C1([PH2](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:31]([CH2:38][C:39](=[O:41])[CH3:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:40][C:39](=[O:41])[CH2:38][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:4][C:3]=1[O:10][CH3:11]

Komponenten

5

Edukt 2

HCID 1183VanillinHCID 178468789HCID 178468789, Verbindung

Produkt 1

HCID 538589221-(4'-Hydroxy,3'-methoxyphenyl)-4-phenoxy-1-butene-3-oneAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Hydroxy-3-methoxybenzaldehyde (2.1 g, 13.8 mMol) and 3-phenoxypropane-2-one triphenylphosphorane (2.8 g, 6.9 mMol) (prepared as described by LeCorre: C. R. Acad. Sci. Paris, 273 81 (1971)) are dissolved in 100 ml of toluene and warmed to reflux. After three hours, the solvent is evaporated and the residue is taken up in tHF. Sodium bisulfite (10.0 g) is dissolved in 100 ml of water and stirred with the solution for one hour. The THF is evaporated and the water is extracted with chloroform. Drying over magnesium sulfate and evaporation of the chloroform gives a yellow oil. Flash chromatography in ethyl acetate on silica gel gives 1.5 g (65%) of 1-(4'-hydroxy,3'-methoxyphenyl)-4-phenoxy-1-butene-3-one; mp=85°-87° C. C, H analysis: Calcd for C17H16O4 (71.81, 5.68); Found (71.85, 5.50).

Aufarbeitung

  1. temperaturewarmed to reflux
  2. customthe solvent is evaporated
  3. dissolutionSodium bisulfite (10.0 g) is dissolved in 100 ml of water
  4. customThe THF is evaporated
  5. extractionthe water is extracted with chloroform
  6. dry with materialDrying over magnesium sulfate and evaporation of the chloroform
  7. customgives a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-b439e6cd35bc49519ea8039f468cc1f0
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05177259

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