Catechol → Benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester

HRID 10616

Reaktionsgleichung

Reaktionsgleichung von HRID 10616
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].Br[C:10](Br)([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:19]([O:18][C:16]([C:10]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1)=[O:17])[CH3:20]

Komponenten

5

Edukt 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl ester

Produkt 1

HCID 12969876Benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl esterAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Ex-1A: Catechol (2.2 g, 20 mmol) was dissolved in acetone. Diethyl dibromomalonate (7.0 g, 22 mmol) and potassium carbonate (2.76 g) were added, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water was added to the residue. The residue was extracted with dichloromethane, and the organic phase was washed with brine, dried over magnesium sulfate and evaporated. Chromatography (hexanes/ethyl acetate, 4:1) gave 3.9 g of benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester. 1H-NMR (CDCl3) δ 6.90–6.97 (m, 4H), 4.37 (q, J=7 Hz, 4H), 1.32 (t, J=7 Hz, 6H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionThe residue was extracted with dichloromethane
  4. washthe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0fb2734542694c16affef6dddddfd246
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094801B2

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