Title of project
Three Step Green Synthesis of Substituted Butenolides Using Copper II Oxide
Faculty Advisor
James Wollack
Department
Chemistry
Three Step Green Synthesis of Substituted Butenolides Using Copper II Oxide
Butenolides are an important groups of chemicals that have a furan ring backbone. They are found in nature in a variety of compounds, with diverse functions. The most well-known butenolide is ascorbic acid, or vitamin C. Here the synthesis of a 2,3,4,4-tetrasubstituted-but-2-ene-4-olide is reported. This three step synthesis starts with the hydration of 3-methylpentyn-3-ol using a mercury II oxide catalyst to form 3-hydroxy-3-methylpentane-2-one. The second step converts this ketone into 2-cyano-3,4-dimethylhex-2-en-4-olide; a lactone, using a Knoevenagel reaction. The final step required an Aldol condensation reaction between 2-cyano-3,4-dimethylhex-2-en-4-olide and anisaldehyde to produce the final product, 2-cyano-4-methyl-3-((1E)-2-(4-methyl-phenyl)ethenyl)-hex-2-en-4-olide. The first step was also attempted using copper II oxide instead of mercury II oxide to make this process "more green."