Tetra(p-hydroxyphenyl)calix[4]resorcine (1), prepared from the acidic condensation of resorcinol with p-hydroxybenzaldehyde in ethanol, was reacted with allyl bromide, ethyl α-chloroacetate or N,N-dipropylchloroacetamide in the system of K₂CO₃/KI/acetone to yield O-alkylation products 2a～2c. Aminolysis of 12 ethoxycarbonylmethoxy groups in 2a with excess 3-(dimethylamino)propylamine, N-benzyl-N-methylamine or triethylenetetramine to yield amide derivatives 3a～3c in high yields. The pyridine-linked amide derivative 3d was prepared successfully by indirect method from 2a in three steps. The structures of all compounds were characterized with elemental analysis, ¹H NMR and IR spectra.

Key words: calix[4]resorcine, calixarene, alkylation, ester, amide