Alkoxy-, Acyloxy-, and Bromomethylation of Resorcinarenes

Reaction of resorcinarene octols with tris-hydroxymethylmethylamine (TRIS), formaldehyde, and alcohols results in tetraalkoxymethylation of
the resorcinol rings. Harsh acylation of aminomethylated resorcinarenes with acid anhydrides leads to the complete acylation of eight hydroxyls
and substitution of the amino versus acyloxy groups. Acyloxymethylated resorcinarene 6b can be transformed into a tetrabromomethylated
derivative 7 through the reaction with HBr in acetic acid.