2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Hydroxy-7-methoxy-5-benzofurancarboxaldehyde

HRID 2419545

Reaktionsgleichung

Reaktionsgleichung von HRID 2419545
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[OH:15][C:16]1[C:24]([CH:25]=[O:26])=[CH:23][C:19]2[CH2:20][CH2:21][O:22][C:18]=2[C:17]=1[O:27][CH3:28]>O1CCOCC1>[OH:15][C:16]1[C:24]([CH:25]=[O:26])=[CH:23][C:19]2[CH:20]=[CH:21][O:22][C:18]=2[C:17]=1[O:27][CH3:28]

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 218565722,3-Dihydro-6-hydroxy-7-methoxy-5-benzofurancarboxaldehyde

Produkt 1

HCID 217856846-Hydroxy-7-methoxy-5-benzofurancarboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

A solution of 817 mg. (3.6 mmole) of DDQ in 10 ml. of dioxane was added to 582 mg. (3 mmole) of 2.3-Dihydro-6-hydroxy-7-methoxy-5-benzofurancarboxaldehyde in 15 ml. of dioxane and the resulting mixture was heated under reflux for 7 hours, cooled and the formed solid removed by filtration. The precipitate was thoroughly washed first with benzene, then with CHCl3. The washings were combined with the initial filtrate and the total concentrated in vacuo to a residue which was chromatographed first on a 20 ml. dry silica gel column (E. Merck 7734) with CHCl3 elution followed by conventional chromatography over 20 g. of silica (E. Merck 7734) packed in benzene-ethyl acetate (95:5) and elution with this solvent mixture provided, after workup, a yellow solid, m.p. 60°-62°.

Aufarbeitung

  1. temperatureunder reflux for 7 hours
  2. temperaturecooled
  3. customthe formed solid removed by filtration
  4. washThe precipitate was thoroughly washed first with benzene
  5. concentrationthe total concentrated in vacuo to a residue which
  6. customwas chromatographed first on a 20 ml
  7. washdry silica gel column (E. Merck 7734) with CHCl3 elution
  8. washelution with this solvent mixture
  9. customprovided

Quellen und Nachweise

ORD-Eintrag
ord-7f35b246bfb64766b166527f289fec84
Quelldatensatz
uspto-grants-1978_08
Patentnummer
US04107182

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