Synthesis of 12-benzyloxy-3,4- dimethoxy-13-methylstilbene and 12- acetoxy-3,4-dimethoxy-13-methylstilbene / Mohd Fadhli Razali

• Main Author: Razali, Mohd Fadhli
• Format: Thesis
• Language: English
• Published: 2008
• Subjects: Immunotherapy. Serotherapy; Pharmacognosy. Pharmaceutical substances (Plant, animal, and inorganic)
• Online Access: https://ir.uitm.edu.my/id/eprint/102036/1/102036.PDF; https://ir.uitm.edu.my/id/eprint/102036/

his research project aims to synthesize a stillbene analogues, 12-benzyloxy-3,4- dimethoxy-13-methylstilbene and 12-acetoxy-3,4-dimethoxy-13-stillbene via series of reactions. This study was carried out in four establish reactions. Firstly, the protection of hydroxyl group of 4-iodophenol, 1 by benzylation and acetylation producing 4-iodo-2-methylphenylbenzylether, 2 and 4-iodo-2-methylphenylacetate, 3. Then, the product from both reaction is used to synthesize the desired compound, 12-benzyloxy-3,4-dimethoxy-13-methylstilbene, 5 and 12-acetoxy-3,4-dirnethoxy- 13-stillbene, 6 by Heck reaction involving the utilization of paladium (II) catalyst, triphenylphosphine ligand, argentum nitrate, potassium acetate and dirnethylformamide solvent. The products were purified by chromatographic technique using thin layer chromatography plate and Prep thin layer chromatography. NMR characterization also had been used in the determination of the structure. The reaction was succesful as both the tentative compound was successfully obtained. 12- benzyloxy-3,4-dimethoxy-13-methylstilbene, 5 and 12-acetoxy-3,4-dirnethoxy- l 3- stillbene, 6 has been synthesized in small amount (20.25% and 26.54% respectively).