Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E,E)-3,3'-(4-Hydroxy-1,3-phenylene)bis-2-propenoic Acid Dimethyl Ester

HRID 1648064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1648064
[CH:1]([C:3]1[CH:10]=[C:7]([CH:8]=O)[C:6]([OH:11])=[CH:5][CH:4]=1)=O.C1(P(=[CH:31][C:32]([O:34][CH3:35])=[O:33])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:35][O:34][C:32](=[O:33])/[CH:31]=[CH:1]/[C:3]1[CH:4]=[CH:5][C:6]([OH:11])=[C:7](/[CH:8]=[CH:31]/[C:32]([O:34][CH3:35])=[O:33])[CH:10]=1

Komponenten

4

Edukt 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 1651064-Hydroxyisophthalaldehyde

Produkt 1

HCID 10706586(E,E)-3,3'-(4-Hydroxy-1,3-phenylene)bis-2-propenoic Acid Dimethyl EsterAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 5.0 g (33.3 mmol) of 5-formylsalicylaldehyde and 24.5 g (73.3 mmol) of methyl (triphenylphosphoranylidene)acetate, in 150 mL of toluene was stirred and refluxed for 2.5 hr and then kept at room temperature overnight. The solvent was removed in vacuo and the solid residue was flash-chromatographed on silica gel. There was obtained 8.07 g (92.5%) of the title compound as a colorless solid.

Aufarbeitung

  1. temperaturerefluxed for 2.5 hr
  2. customThe solvent was removed in vacuo
  3. customthe solid residue was flash-chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8fede513cd3343d6946eca2c2d6cd77c
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05434186

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