Synthesis of 2, 3-Methylenedioxynaphthalene

Abstract

2, 3-Methylenedioxynaphthalene (VIII), mp 97-99°, which was first isolated from Cinnamomum camphora SIEB., was synthesized from piperonal (I) via seven steps. In the course of this study, reduction of V to VI was successfully achieved by PdCl₂-NaBH₄ without affecting the carboxyl group. All spectra data (ultraviolet, infrared, mass) of synthesized VIII were almost identical with those of natural product and its nuclear magnetic resonance spectrum also agreed with the structure of VIII. As a result, the structure of natural VIII was synthetically confirmed.