A thesis submitted in fulfilment of the requirements for the degree Magister Technologiae (Chemistry) in the Faculty of Applied Sciences, Department of Chemistry, Cape Peninsula University of Technology, 2008 / Green et al. attempted to synthesize linear naphthopyranquinones from a naphthyl dioxolane using a TiCl4 as a catalyst. They managed to synthesise an angular naphthopyran as well as a linear naphthopyran in low yield. They showed that reducing the steric strain at position 1 of the naphthyl dioxolane afforded a low percentage yield of the linear naphthopyran plus an angular one. This thesis describes the synthesis of linear naphthopyrans with an improved percentage yield using TiCl4 as a catalyst. This was achieved by placing a OMe group of less steric hinderance at position 1 and a Br atom at position 4 of a naphthyl dioxolane. The OMe group at position 1 was to allow isomerisation to occur at position 2, and the Br atom was to inhibit isomerisation at position 4, thereby inhibiting the formation of the angular naphthopyran.