Five 2-(2-heterocycle-2-ylthioethoxy)ethanols 1a～1e were prepared by the reaction of 2-(2-chloroethoxy)ethanol and 2-mercapto-heterocycles using sodium iodide as catalyst. Consequently, the compounds 1a～1e reacted with tosyl chloride to afford corresponding tosylates 2a～2e. A series of p-tert-butylcalix[4]arene derivatives 3a～3e which contain heterocycle functional groups tethered by ether bridges were easily synthesized by the reaction of p-tert-butylcalix[4]arene with tosylated 2a～2e in the presence of potassium carbonate, respectively. All new compounds were characterized by ¹H NMR, ¹³C NMR, IR, MS techniques and elemental analysis. Meanwhile, the structures of calix[4]arene derivatives 3a, 3b and 3d were identified by X-ray diffraction analysis.

Key words: calix[4]arene, 2-mercapto-heteroaromatic compound, synthesis, crystal structure