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In this study we report the synthesis of cyclobutanediol monomers as potential replacements for bisphenol-A (Scheme 1). Key to monomer synthesis is the creation of the cyclobutane ring, which is formed by the dimerization of two ketene (C=C=O) functionalities. However, the reactive nature of the ketene requires protection prior to dimerization. A Meldrum’s acid derivative was used as a protecting group; thermolysis of this group yields the ketene along with the evolution of carbon dioxide and acetone. Using this chemistry, two different alcohol monomers have been synthesized: bisphenol cyclobutanedione 5 and bisphenol cyclobutanediol 6. The polymerization of 5 proved difficult; therefore, current work involves scaling up the synthesis of 6. Using protection group chemistry to mask either the secondary or phenolic alcohols from polymerization conditions will allow formation of multiple polyethers, polyesters, and polycarbonates. Further characterization of the physical and mechanical properties of these polymers will determine whether cyclobutanediol monomers can replace bisphenol-A in conventional polymers.