P-(BENZYLOXY)CALIX[8]ARENE - ONE-POT SYNTHESIS AND FUNCTIONALIZATION

The condensation of hydroquinone monobenzyl ether in the presence of s everal bases gives a mixture of cyclic oligomers. Using p-benzyloxyphe nol, paraformaldehyde, and NaOH in 45:82:1 molar ratio in refluxing xy lene, p-(benzyloxy)calix[8]arene (2) was selectively produced in 48% i solated yield. Compound 2 was also functionalized at the lower rim wit h acetoxy, methyl, pentyl, [(ethyloxy)carbonyl]methyl, and [(N,N-dieth ylamino)carbonyl]methyl groups. Replacement of the benzyl groups on th ese compounds allowed for the first time the high-yield syntheses of c alix[8]hydroquinone and its derivatives.