Of Egcg Intermediate 3,4,5 - Three Benzyloxy Cinnamyl Alcohol Synthesis

3,4,5-Tris(benzyloxy)cinnamyl alcohol was synthesized from methyl 3,4,5-tris(hy-droxy)benzoate according to a five step synthetic route. Treatment of methyl 3,4,5-tris(hy-droxy)benzoate with benzyl chlorine gave methyl 3,4,5-tris(benzyloxy)benzoate in 84% yield. Reduction of the resulting benzyl protected carboxylic ester with Lithium aluminium hydride in anhydrous condition gave the corresponding alcohol in 73% yield. Oxidation of the alcohol with PCC/Al₂O₃ or oxygen gave 3,4,5-tris(benzyloxy)benzaldehyde in 77% and 76% yield, respectively. 3,4,5-tris(benzyloxy)cinnamate was obtained in 91% yield by reaction of 3,4,5-tris(benzyloxy)benzaldehyde with triethyl phosphonoacetate in the presence of sodium hydride. Reduction of 3,4,5-tris(benzyloxy)cinnamate gave the final product 3,4,5-Tris(benzyloxy)cinnamyl alcohol in 92% yield. Structure and purity of the intermediates and the final product were determined by ¹H NMR and HPLC.