The calixarene macrocyclic framework continues to attract attention as a starting point for the development of cation receptors. Recently, various cavitand derivatives have been synthesized as host compounds for metal ion recognition, anione recognition, anione recognition, and organic guests. We report the syntheses of four different cavitand derivatives containing four xylenyl group and benzimidazoyl groups utilizing tetrahydroxy cavitand as an intermediate for these syntheses. Their structures were assigned on the basis of various spectroscopic studies