Programme Book - UPM - Universiti Putra Malaysia

P02DERIVATIVES OF VANILLINN.A. Rasid, N.A. Md Saad, S.M. Mohd Nor*Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPMSerdang, Selangor, MalaysiaCorresponding author: smariam@upm.edu.myVanillin (4-hydroxy-3-methoxybenzaldehyde) is a pleasant smelling aromaticcompound formed through enzymatic breakdown of glucose during the curing processof the vanilla bean. It is widely used as a flavoring additive for cooking and infragrances. Vanillin can undergo many steps of synthesis; methylation, reduction andnucleophilic addition. The synthesis of 3,4-dimethoxybenzylalcohol from vanillinunderwent two steps, (1) methylation of vanillin and (2) reduction of methylationproduct. The second pathway was doing the steps vice versa, meaning (1) reduction ofvanillin followed by (2) methylation of reduction product. The synthesis of iminefrom vanillin underwent nucleophilic addition reaction between carbonyl group(vanillin) and amine (butylamine and propylamine). Two new series of differentamino substituted aldehydes with general formula, R 1 -CH=NR 2 were produced. Theproducts were analyzed by means of 1 H NMR, 13 C NMR, and GCMS. As a result, themethylation of vanillin produced purple crystals with 87.7% yield of vetaraldehyde.The reduction of vetaraldehyde produces 3,4-dimethoxybenzylalcohol as a dark bluesolid in low yields. Reduction of vanillin formed a vanillyl alcohol as solid yellowcrystal with 70.3% yield. For nucleophilic addition of vanillin, 2-methoxy-4-[(E)-(propylimino)methyl]phenol and 4-[(E)-(butylimino)methyl]-2-methoxyphenol wereobtained as purple and orange crystals respectively.17 |16 th Industrial Chemistry Seminar: Chemistry- A Passport to a Brighter Future