The naphthylisoquinoline family of natural products exhibit antifungal, antimalarial, and antiviral activities, while140 naphthylisoquinoline alkaloids have been identified, only a select few have been isolated from Ancistrocladus cochinchinensis. This plant has been used in folk medicine as a diuretic, antifebrile, and antiphlogistic, indicating that these alkaloids are promising candidates for medicinal applications. The pharmaceutical industry is always seeking a wider selection of treatments for specific malarial and viral infections. A convergent synthesis of 4’-O demethylhamatine will facilitate the preparation of naturally occurring napthylisoquinoline alkaloids, and synthetic derivatives for medicinal screening. The preliminary step in the total synthesis begins with the mono demethylation of 1-chloro-3, 5-dimethoxybenzene. Demethylation provides the precursor needed for the secondary step, benzylation. Though several approaches to the mono-demethylation of bismethoxy-benzenes have been reported, the conditions often lead to bis-demethylated products. The focus of this work is to evaluate these known strategies and determine the optimum conditions for preparation of the key intermediate, 3-chloro-5-methoxyphenol.