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https://doi.org/10.37358/Rev.Chim.1949

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Revista de Chimie (Rev. Chim.), Year 2003, Volume 54, Issue 4,





The Synthesis of 5-Formyl-Ethyl-Vaniline and of Some Derivatives with a Possible Biological Activity
Anca Nicolae, Constantin Draghici, Adriana David


Abstract:

The 4-hydroxy-5-ethoxyisophtalic aldehyde (5-formyl ethyl vaniline) was synthesized by Duff reaction from ethyl-vaniline and hexamethylenetetramine. The dialdehyde was condensed with nitrogen bases (hydroxilamine, o-methylhydroxilamine, N,N-dimethylhydrazine) resulting in the corresponding dioxine, o-methyldioxime and N,N-methylhydroxilamine. In the reactor of the dialdehyde with acetylacetone or malonic ester in the molar ratio 1:1 between reactants, it is observed a higher reactivity of the formyl group from the orto position of the hydroxyl group. 5-Formyl ethyl vaniline was condensed with an ethyl cyanoacetat excess and the product resulted by heating in an acid environement transforms into a cumarinic derivative. The structure of the synthesized compounds was confirmed by spectral methods (IR, 1H-NMR, 13C-NMR). Keywords: 5-formyl ethyl-vaniline, dialdehyde, Duff reaction


Issue: 2003, Volume 54, Issue 4
Pages:
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