Vanillin → Methyl Ferulate

HRID 250854

Reaktionsgleichung

Reaktionsgleichung von HRID 250854
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O=[CH:26][C:27]1[CH:35]=[CH:34][C:32]([OH:33])=[C:29]([O:30][CH3:31])[CH:28]=1>C1(C)C=CC=CC=1>[OH:33][C:32]1[CH:34]=[CH:35][C:27](/[CH:26]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:28][C:29]=1[O:30][CH3:31]

Komponenten

4

Edukt 2

HCID 1183VanillinHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Produkt 1

HCID 5357283Methyl FerulateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

6.5 g (19.5 mmol, 3 eq) of methyl triphenylphosphoranylideneacetate are added to a solution of 1.0 g (6.5 mmol, 1 eq) of vanillin in 15 ml of toluene. The reaction mixture is stirred for 1 hour at 90° C. The solvent is evaporated off and the residual oil is then chromatographed on silica gel (8/2 heptane/ethyl acetate). 1.12 g of methyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate are obtained in oil form. Yield=83%

Aufarbeitung

  1. customThe solvent is evaporated off
  2. customthe residual oil is then chromatographed on silica gel (8/2 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a2863b5cce64477b925e70887b3e9238
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863332B2

Verknüpfte Notizen

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