Improved Synthesis of Larger Resorcinarenes

The synthesis of the larger resorcin[5 and 6]arene macro cycles [5](OMe) and [6](OMe) has been realized by a Lewis acid catalyzed condensation of 1,3-dimethoxy-2-methylbenzene with paraformaldehyde in o-dichlorobenzene as the solvent. The methoxy-resorcin[5 and 6]arenes were quantitatively demethylated by treatment with BBr3 to obtain the corresponding macrocycles with free OH groups. X-ray studies showed that in the solid state both the conformation and the packing of [6](OMe) and [5](OMe) are driven by C-H center dot center dot center dot O, C-H center dot center dot center dot pi, and pi center dot center dot center dot pi interactions.