SYNTHESIS AND NMR STRUCTURE DETERMINATION OF NEW LINEAR GERANYLPHENOLS BY DIRECT GERANYLATION OF ACTIVATED PHENOLS
The known geranylhydroquinone 2, geranylorcinol 4 and the derivative (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-methylbenzene-1,3-diol 5, were prepared by Electrophilic Aromatic Substitution (EAS) reactions between the corresponding phenol derivatives containing electron-donor subtituents and geraniol us...
Guardado en:
| Autores principales: | , , , , , , , , |
|---|---|
| Lenguaje: | English |
| Publicado: |
Sociedad Chilena de Química
2013
|
| Materias: | |
| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072013000200033 |
| Etiquetas: |
Agregar Etiqueta
Sin Etiquetas, Sea el primero en etiquetar este registro!
|
| Sumario: | The known geranylhydroquinone 2, geranylorcinol 4 and the derivative (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-methylbenzene-1,3-diol 5, were prepared by Electrophilic Aromatic Substitution (EAS) reactions between the corresponding phenol derivatives containing electron-donor subtituents and geraniol using BF3XOEt2 as a catalyst. In addition, spectroscopic NMR information for 4 and 5 is complemented. Furthermore, the new (E)-2-(3,7-dimethylocta-2,6-dienyl) benzene-1,3,5-triol (geranylphloroglucinol) 13, (E)-2-(3,7-dimethylocta-2,6-dienyl)-1,3,5-trimethoxybenzene 14, (E)-2-(3,7-dimethylocta-2,6-dienyl)-6-methoxyphenol 15, (E)-3-(3,7-dimethylocta-2,6-dienyl)-2-methoxyphenol 16, (E)-5-(3,7-dimethylocta-2,6-dienyl)-2-methoxyphenol 17, (E)-4-(3,7-dimethylocta-2,6-dienyl)benzene-1,3-diol 18, (E)-3-(3,7-dimethylocta-2,6-dienyl)benzene-1,2-diol 19, (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-isopropyl-2-methylphenol 20, (E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isopropyl-3-methylphenol 21, (E)-2-(3,7-dimethylocta-2,6-dienyl)-4-isopropyl-5-methylphenol 22, and(E)-2-tert-butyl-4-(3,7-dimethylocta-2,6-dienyl)-5-methylphenol 23 were also prepared with this synthesis strategy. All the synthesized compounds were fully characterized and their structures were established by IR, MS and mainly NMR spectroscopic dates. |
|---|