Synthesis of 4-acetoxy-12-benzoyloxystilbene / Mohd Firdaus Sanusi

This research project aims to synthesize a stilbene analogue, 4-acetoxy-12- benzoyloxystilbene 1 via series of reactions. This study was carried out in four established reactions. Firstly, starting from 4-iodophenol, the substance undergo protection of hydroxy 1 group into 4-iodophenylbenzoate. Then another starting material, 4-hydroxybenzaldehyde was protected by adding the acetoxy group to produce 4- acetoxybenzaldehyde followed by the Wittig reaction to develop 4-acetoxystyrene. The product from the Wittig reaction and 4-iodophenylbenzoate is utilized to synthesize the desired compound, 4-acetoxy-12-benzoyloxystilbene 1 by Heck reaction that involves the use of palladium (II) catalyst, triphenylphosphine ligand, argentum nitrate, potassium acetate and dimethylformamide solvent The products were purified by chromatographic technique by the use of thin layer chromatography plate. UV spectrophotometer and NMR characterization also had been used in the determination of the structure. However, the expected compound to be synthesized were not successfully obtained. Instead an almost structurally identical compound has been synthesized in small amount (18.8%).