Lignin is a polymer found in plant fibers that is a promising alternative to crude oil as a source of aromatic carbon compounds. Previous work has shown successfully developed methods for the catalytic depolymerization of lignin into an aldehyde and subsequent aldehyde trapping by formation of an acetal. With the goal to investigate applications of this lignin depolymerization process to tandem reactions, we synthesized a model compound, 2-(2-methoxyphenoxy)-1-phenylethan-1-ol, for lignin and sought to optimize the first step for catalytic depolymerization. Replication of the former catalytic depolymerization and aldehyde trapping reaction was initially carried out to ensure effective results. Then, alternative conditions for depolymerization were attempted by allowing the lignin model compound to react using various metal triflate catalysts, solvents, reaction temperatures, and reaction times. The target products for some trials were not observed using <sup>1</sup>H NMR spectroscopy or mass spectrometry, which was attributed to the quick repolymerization of aldehyde and/or lack of consumption of starting material, depending on the reaction conditions. Nonetheless, we were successful in finding a few reaction conditions that indicated progress towards our goal of using lignin depolymerization for sustainable applications.

Synthesis of a model compound for lignin and investigating catalysts for depolymerization

255th National Meeting (2018)

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