Synthesis Of Resveratrol

Resveratrol possesses many pharmacological activities, such as, anticancer, antioxidation, antibacterial, blood lipid-lowing and so on. Because of the high cost of extracting from plants and by biosynthesis, researchers pay much attention on the chemical synthesis of resveratrol. While there are several methods of chemical synthesis of resveratrol, we employed Wittig reaction to synthesize resveratrol,3,5-dihydroxy toluene was used as starting material,which reacted with acetic anhydride to afford 3,5-diacetoxy toluene(3.4).3.4 reacted with N-bromosuccinimide (NBS) in CCl4 to get 3,5-diacetoxybenzyl bromide(3.5).3.5 reacted with PPh3 in toluene to generate triphenyl(3,5-diacetoxybenzyl) phosphonium bromide(4.1). The Wittig reaction between 4.1 and 4-methoxy benzaldehyde in the presence of CH3ONa, three products were obtained, i.e.,3,5-diacetoxy-4'-methoxystilbene(4.3), 3-acetoxy-5-hydroxy-4'-methoxystilbene (4.4) and 3,5-dihydroxy-4'-methoxystilbene(4.5), when the molar ratio of 4.1:CH3ONa=1:1-1.5. If the molar ratio of 4.1:CH3ONa=1:3, then the product was only one., i.e.,3,5-dihydroxy-4'-methoxystilbene(4.5). Resveratrol was obtained by the demethylation of 4.5 with BBr3.