Progress Toward the Synthesis of a Naphthoquinone

Naphthoquinones are organic compounds naturally found in plants that have multiple medical benefits such as antimicrobial activity against methicililin-resistant Staphylococcus aureus (Machado et al., 2003), or anti-tumor activity against cancer cell lines (Lee et al., 2007). One way to synthesize 2-acetyl-1-4-naphthoquinone involves Friedel-Crafts acylation of 1-naphthol to produce 2-acetyl-1-naphthol, which is nitrated to give 2-acetyl-4-nitro-1-naphthol (Green, 1982). The synthetic pathway of 2-acetyl-1-4-naphthoquinone reported here takes 4 steps to complete but only three steps were completed to yield a precursor, 2-acetyl aminophenol, to the desired product. In step 2, the substitution of nitric acid with hydrogen peroxide provided a more environmentally friendly production process.