Study On Catalyzed Ortho-formylation Of Phenols

Salicylaldehydes compound have a wide range of applications in medicine, pesticide, dyes and essence as an important intermediate in industry of fine chemicals. Especially salicylaldehyde not only in medicine, dyes, agricultural pesticides, spices has a wide range of applications, but also can form salen ligands complex. And it is widely used in vinyl epoxylation, asymmetric cyclopropanation, kinetic resolution, asymmetric cyanosilylane, Diels-Alder cycloaddition and other fields.In this study, we have synthesized a series of salicylaldehydes from phenol and substituted phenols. We through analysis of reaction and do a lot of research finally get a new type of improved Metal ion catalyst method, compared with the literature that the method has the advantage of mild reaction condition; the yield is much higher than original method. In this way a series of salicylaldehydes was synthesized, such as3,5-di-t-butylsalicylaldehyde,5-tert-butylsalicylaldehyde,5-chlorosalicylaldehyde,5-methoxysalicylaldehyde,5-methyl-salicylaldehyde,5-nitrosalicylaldehyde,2-hydroxynaphthaldehyde, Ethyl3-formyl-4-hydroxylphenylacetate,3-acetylaminosalicylaldehyde,3-t-butyl-2,5-dihydroxybenzaldehyde.Four salicylaldehydes, salicylaldehyde,5-methoxysalicylaldehyde,3,5-di-t-butyl-salicylaldehyde, and5-nitrosalicylaldehyde, were also synthesized by Duff reaction, compared with Metal ion catalyst method.Substituted salicylaldehyde were synthesized using substituted phenols and paraformal-dehyde as starting materials with Lewis acid as catalyst and triethylamine as the deacid reagent. The influences of catalysts, ratio of catalyst and substrate, reaction temperature and reaction time on the yield are investigated. And compounds were certified by NMR spectra and they were the target compounds.