Reaktionsgleichung
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12]C)=[CH:6][C:3]=1[CH:4]=[O:5].[OH-].[Na+].CCCCCC.CCOC(C)=O>OS(O)(=O)=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[CH:6][C:3]=1[CH:4]=[O:5]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
2-Chloro-4,5-dimethoxybenzaldehyde (5.00 g, 24.9 mmol; commercially available from Akos Consulting) is dissolved at room temperature in conc. H2SO4 (23 mL; Riedel) at room temperature. The deeply colored mixture is heated at 65° C. overnight with stirring, and after cooling is poured with caution into ice-water containing 38 g of solid NaOH (pH 14). The water phase is washed twice with AcOEt, and then is adjusted to pH 1 by addition of HCl 37% with ice-cooling to form a white suspension. Extraction with AcOEt, drying of the organics over MgSO4 and evaporation gives the crude product in a mixture with unreacted starting material. The title compound is obtained after silica gel chromatography (hexane/AcOEt gradient from 3:1 to 1:1) as white solid. TLC, Rf (hexane/AcOEt 1:1)=0.35. MS: 187.0 [M+H]+. ]+. 1H-NMR (DMSO-d6): δ 3.41 (s, 3H), 7.14 (s, 1H), 7.45 (s, 1H), 9.83 (s, 1H), 10.2 (s, 1H) ppm.
Aufarbeitung
- temperatureafter cooling
- washThe water phase is washed twice with AcOEt
- additionis adjusted to pH 1 by addition of HCl 37% with ice-
- temperaturecooling
- customto form a white suspension
- extractionExtraction with AcOEt
- customdrying of the
- customorganics over MgSO4 and evaporation
- customgives the crude product in a mixture
Quellen und Nachweise
- ORD-Eintrag
- ord-d128e6b819514f98b801f69f1dfdd085
- Quelldatensatz
- uspto-grants-2010_10
- Patentnummer
- US07807709B2
Verknüpfte Notizen
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