2,2-Dimethyl-1,3-dioxane-4,6-dione → 5-((3-Hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Reaktionsgleichung

[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.[OH:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[NH2:15].[CH:21]([O-])([O-])OC>>[OH:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][CH3:20])[NH:15][CH:21]=[C:6]1[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:5]

Komponenten

Edukt 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

HCID 743145-Amino-2-methoxyphenol

HCID 53629101Methylorthoformate

Produkt 1

HCID 226465515-((3-Hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dioneAusbeute 82 %

Versuchsvorschrift

A solution of Meldrum's acid (32 g, 22.2 mmol)in methyl orthoformate (200 ml) was stirred at 100° C. 3-Hydroxy-4-methoxyaniline (28 g, 20 mmol) was added and the solution was heated at reflux for 15 minutes. After cooling, the mixture was stirred overnight at ambient temperature. The precipitate was collected by filtration, washed with methyl orthoformate followed by ether and dried under vacuum to give 5-((3-hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (47.5 g, 82%).