In this work, synthesis, characterization, and antioxidant activities of two Schiff base monomers (1 and 2) and their corresponding oxidation products (3 and 4) were reported. The monomers were prepared by condensation of 8-amino-2-naphthol with 2,4-dihydroxybenzaldehyde and 3,4-dihydroxybenzaldehyde, and then, they were oxidized to in alkaline medium by NaOCl to obtain the corresponding oxidation products. The compounds 1-4 were characterized by various spectral techniques. The analysis results indicated that the oxidation products had a chain structure consisting of randomly ordered phenylene and oxyphenylene units. In vitro antioxidant activities of 1-4 were evaluated against a ABTS cation radical and a DPPH free radical and compared with standard natural antioxidants, vitamin C (ascorbic acid), and vitamin E (alpha-tocopherol). The ferric reducing antioxidant power and ferrous-ion chelating activities of 1-4 were also determined.