Sodium Hydroxide → HCID 69795215, Verbindung

HRID 2181661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181661
[CH:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:6]=2[CH:7]=1)=[O:2].[OH:16]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+].[OH-].[Na+]>CS(C)=O.O>[CH3:15][O:14][C:12]([C:10]1[CH:9]=[CH:8][C:6]2[CH:7]=[C:3]([C:1]([OH:16])=[O:2])[O:4][C:5]=2[CH:11]=1)=[O:13]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 516951Monobasic potassium phosphateHCID 22481722588702-95-8HCID 23668197Sodium Chlorite

Produkt 1

HCID 69795215HCID 69795215, VerbindungAusbeute 289,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Methyl 2-formyl-1-benzofuran-6-carboxylate (1.23 g, 6.0 mmol) is dissolved in DMSO (12 ml). KH2PO4 (229 mg, 1.68 mmol) in H2O (2 ml) and NaClO2 (80%, 949 mg, 8.4 mmol) in H2O (12 ml) are added drop-wise to the solution, and the reaction is stirred over the weekend at RT. The pH is adjusted to 10 with 2N NaOH and the mixture is extracted with Et2O (3×50 ml). The pH is adjusted again to 3 with concentrated HCl and the slurry is filtered. The cake is dried overnight, yielding 1.07 g (81%) of 6-(methoxycarbonyl)-1-benzofuran-2-carboxylic acid as an ivory solid. HRMS (FAB) calcd for C11H8O5+H: 221.0450, found 221.0436 (M+H)+.

Aufarbeitung

  1. extractionthe mixture is extracted with Et2O (3×50 ml)
  2. filtrationthe slurry is filtered
  3. customThe cake is dried overnight

Quellen und Nachweise

ORD-Eintrag
ord-dfd74f79afd14164b8f2737a18ad798c
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894042B2

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