Methanol → 1,2-Bis(3,4-dihydroxyphenyl)ethane-1,2-dione

HRID 2109647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2109647
C1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]([C:12]([C:14]3[CH:19]=[CH:18][C:17]4[O:20]C[O:22][C:16]=4[CH:15]=3)=[O:13])=[O:11])=[CH:4][C:3]=2[O:2]1.B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:10]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([OH:22])[CH:15]=2)=[O:13])=[O:11])[CH:6]=[CH:7][C:8]=1[OH:9]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 25134Boron tribromideHCID 2263391,2-Bis(1,3-benzodioxol-5-yl)ethane-1,2-dione

Produkt 1

HCID 2382321,2-Bis(3,4-dihydroxyphenyl)ethane-1,2-dioneAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of bis(3,4-methylenedioxy)benzil (500 mg) in dry CH2Cl2 (50 ml) under nitrogen, was slowly added boron tribromide (1.6 ml) then stirring continued for a further 3.5 hours. Methanol (100 ml) was added carefully, then the solvent evaporated in vacuo to a volume of 1 ml, this addition and evaporation was repeated twice more. The product was purified by column chromatography over silica gel when elution with diethylether in dichloromethane gave 3,4,3′,4′-tetrahydroxybenzil (217 mg, 47%) as a yellow powder.

Aufarbeitung

  1. customthe solvent evaporated in vacuo to a volume of 1 ml
  2. additionthis addition and evaporation
  3. customThe product was purified by column chromatography over silica gel when elution with diethylether in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e658ef01f62f4b5c8a713a50ab81ba01
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514583B2

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