Ethanol → 2-Phenyl-2H-1,2,3-triazole-4,5-dicarboxylic acid

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Reaktionsgleichung

CC1[C:3]([C:13]([OH:15])=[O:14])=[N:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[OH-:16].[Na+].[O-][Mn](=O)(=O)=O.[K+].[CH2:24]([OH:26])[CH3:25]>O>[C:7]1([N:5]2[N:6]=[C:25]([C:24]([OH:16])=[O:26])[C:3]([C:13]([OH:15])=[O:14])=[N:4]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: 23 °C

Versuchsvorschrift

A solution of 5-methyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid (10.2 g, 50 mmol) and NaOH (17.6 g, 440 mmol) in water (375 mL) at 23° C. was treated with KMnO4 (30.8 g, 195 mmol). The resulting solution was heated at reflux for 17 h, cooled to 23° C. and treated with ethanol (50 mL). The resulting mixture was filtered to remove MnO2. The filtrate was acidified with HCl (conc.) to pH 1. The resulting white solid was collected by filtration. The filtrate was concentrated to half volume and more solid was collected by filtration. The two combined batches of solid were dried in vacuo to afford 11.1 g (95%) of 2-phenyl-2H-1,2,3-triazole-4,5-dicarboxylic acid.

Aufarbeitung

temperatureThe resulting solution was heated
temperatureat reflux for 17 h
filtrationThe resulting mixture was filtered
customto remove MnO2
filtrationThe resulting white solid was collected by filtration
concentrationThe filtrate was concentrated to half volume and more solid
filtrationwas collected by filtration
customThe two combined batches of solid were dried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-7b3667eafbd842b18f609f673d048241
Quelldatensatz: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06974813B2

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