Synthesis of 4-alkoxypyridines as intermediates for zwitterionic liquid crystals

Abstract

A series of 4-alkoxypyridines with n = 5–18 was obtained in typical yields of 75-80% by reacting 4-chloro-pyridine hydrochloride with the appropriate alcohol in DMSO in the presence of powdered NaOH. The reported synthesis is compared to other methods for preparation of 4-alkoxypyridines, and their uses are reviewed. 4-Tridecyloxypyridine is converted into the bis-zwitterionic derivative of [closo-B10H10]2-, which exhibits liquid crystalline and soft crystalline phases. The solid-state structures of two pyridines and the bis-zwitterion are established by the single crystal XRD method. The effect of N-atom coordination on the pyridine ring geometry is investigated.