Synthesis of Resorcinarene with Modified Functionality

Cavitands are being extensively research due to the capability of these molecules to polymerize, catalyze, and encage guest molecules of complementary size and shape. Resorcinarenes, a particular type of cavitands, are cyclic tetramers formed by an acid catalyzed condensation reaction of resorcinol with aldehydes. Functionality can be added to resorcinarene derivatives by using different reactants, which would give the molecule a variety of new chemical applications. In this experiment trans-2,4-dimethoxy cinnamic acid was methylated to form an ester and catalyzed by boron trifluoride etherate (BF3*O(C2H5)2) to make the resorcinarene. The reduction of this tetra ester resorcinarene would add new functionality, selectively to the lower rim. This highly efficient scheme indicates that this tetramer has potential as a precursor to form novel compounds