Partial Etherification Reactions of Cavitand Phenol Bowls

Abstract

Reactions between the C₄v-symmetrical cavitand tetraphenol (2), various bases, and less than 4 molar equivalents of alkyl halides result in the generation of statistical mixtures of the five possible ether products along with unreacted starting material. Useful quantities of monoalkoxytriphenol (8), A,B-dialkoxydiphenol (9) and trialkoxymonophenol (11) are obtained by controlling the reaction stoichiometry and the desired products can, in general, be isolated by straightforward chromatographic means.