The Synthesis of Selectively Substituted p-Acethylcalix[4]arene

A method is described for the selective functionalization of calix[4]arene at the para positions of the phenyl rings. The diametrically substituted calix[4]arene dimethyl ether 3, obtained from the treatment of calix[4]arene 2 with methyl iodide in the presence of $K_2CO_3$, is converted to the diacetyloxy calix[4]arene dimethyl ether 4. This compound undergoes Fries rearrangement to yield the diametrically p-diacetylcalix[4]arene dimethyl ether 5 in 68% yield.