Multistep Synthesis of a 3(2H)-Furanone Featuring a Green Aldol Condensation

Abstract

A multistep synthesis of a novel arylidene 3(2H)furanone has been designed and optimized for the second-year organic laboratory. The three-step sequence consists of a nucleophilic substitution, intramolecular cyclization, and acidcatalyzed aldol condensation, and can be carried out within two 3 h laboratory periods. The final product is a crystalline solid that does not require purification and bears structural resemblance to natural products with medicinal properties. Reactions are performed at room temperature, and the aldol condensation takes place without the need for organic solvent, providing students hands-on experience with chemical transformations that illustrate green chemistry principles.