Starting with readily available p-tert-butylcalix[4]arene 3 tert-butyl groups are removed by $AlCl_3$-catalyzed de-alkylation reaction, and the calix[4]arene 4 formed is converted into the tetraacyl esters. These compounds undergo Fries rearrangement to yield p-acylcalix[4]arenes. p-Acetyl, p-propionyl, p-butyryl, and p-benzoylcalix[4]arene 10, 11, 12 and 14 are synthesized in 70-80% yields by treatment of the corresponding esters 5, 6, 7 and 9 with $AlCl_3$ in nitrobenzene. When the tetraisobutyryl ester 8 was treated with the same condition, only two isobutyryl groups were rearranged to the para-positions of calix[4]arene, and remaining two groups were simply cleaved.
