Lignin is a complex organic polymer that's found in the cell wall of plants. It's a hydrophobic molecule with a molecular weight over 10,000 g/mol. Each lignin polymer is made up of three lignin monomers: coniferyl alcohol (4-hydroxy-3-methoxycinnamyl alcohol), sinapyl alcohol (4-Hydroxy-3,5-dimethoxycinnamyl alcohol), and coumaryl alcohol (4-hydroxycinnamyl alcohol). We are interested in exploring the redox properties of these monomers and hence we require a few grams of each. These lignin monomers are relatively expensive and hence to sustain this research, we have begun by synthesizing coumaryl alcohol from its carboxylic acid precursor coumaric acid. This synthesis is a 2-step process 1) the carboxylic acid is converted to the ethyl ester and 2) the ester is reduced to the alcohol. The reaction was monitored using HPLC and the products were characterized using mass spectrometry and NMR.

Synthesis of coumaryl alcohol: A lignin monomer

ACS Spring 2022

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