Calixarenes. 7. p-Phenycalixarene

Article abstract of DOI:10.1021/jo00135a005

p-Phenylcalix<4>arene (11), in the cone conformation, is a basket-shaped compound containing a large cavity and, therefore, is of interest for studies of host-guest complexation.Its unequivocal synthesis has been achieved by the stepwise method of Hayes and Hunter, by starting with 2-bromo-4-phenylphenol and adding methylene and p-phenylphenol groups sequentially until a linear tetramer (9) is attained.Removal of the bromine followed by acid-catalyzed cyclization yields the calixarene 11, along with two other materials that are presumed to be the isomeric macrocyclic compounds 12 and 13. p-Phenylcalix<4>arene synthesized in this fashion is different from the compound reported by Zinke from the condensation of p-phenylphenol and formaldehyde in the presence of base, and it appears that 11 is not a major product, and perhaps not even a minor product, of that reaction mixture.