Synthesis of a Novel Nitrile Cavitand

The synthesis of a nitrile cavitand was accomplished in four steps. The first step was an acid-catalyzed dehydration between acetaldehyde and 2-methyl resorcinol to form a resorcin(4)arene. The second step was a cavity forming reaction via etherification. The third step of the synthesis involved a radical benzylic bromation using NBS, with AIBN as a catalyst. The final step was an SN2 reaction with a cyano as the nucleophile. Future goals are to use the nitrile cavitand for metal coordination and further functionalization