Role of alkali and alkaline earth ions on the formation of calix[4]arene-amide derivatives through O-alkylation of the lower rim phenolic-OH groups in general and template action of K + in particular have been explored. Na + and K + ions among alkali, and Ca 2+ and Sr 2+ ions among alkaline earth have shown tetra-amide derivatives bound to metal ion species. Among all these, potassium salts act as template and yields a K + bound tetra-amide derivative where the charge is counter balanced by a calix [4] arene-monoanion and the product is crystallographically characterized. Change in the amide precursor used in these O-alkylation reactions has no effect on the type of the amide derivative formed. Also demonstrated is a direct one-step reaction for the preparation of 1,3-di-amide derivative in high yield and low reaction period using CsHCO 3 .Keywords. O-alkylation at the lower rim of calix[4]arene; template action of K + ; mono-anion of p-tertbutyl-calix[4]arene; alkali and alkaline earth ions.