2-Methoxy-4-[5-(2-oxo-1,3-dioxolan-4-yl)-4,5-dihydroisoxazol-3-yl]phenyl 4-n-decyloxybenzoate

This study addresses the synthesis of a new liquid crystalline compound featuring a 3,5-disubstituted isoxazoline and a 1,3-dioxolan-2-one ring, and renewable aromatic building blocks derived from vanilin and benzoic acid. The target compound was synthesized through a multistep synthetic route involving alkylation, esterification, oxime formation, and a 1,3-dipolar cycloaddition reaction. The synthesized compound, 2-methoxy-4-[5-(2-oxo-1,3-dioxolan-4-yl)-4,5-dihydroisoxazol-3-yl]phenyl 4-n-decyloxybenzoate, was isolated and fully characterized by spectroscopic techniques. Liquid crystal behavior was evaluated by DSC and POM. The monotropic mesomorphic behavior of the title compound was dictated by the interplay between molecular architecture and intermolecular organization, with the methoxy substituent and the 1,3-dioxolan-2-one ring critically influencing phase stability and texture morphology. These findings suggest a structure–property relationship and guide ongoing synthetic optimization toward achieving a stable enantiotropic liquid-crystalline phase and further ion-conduction experiments.