Endo cis-4-cyclohexane-1,2-dicarboxylic anhydride Synthesis through Diels-Alder

Endo cis-4-cyclohexane-1,2-dicarboxylic anhydride Synthesis through Diels-Alder

Three common reactions covered in undergraduate organic chemistry courses are Diels-Alder addition, carbonyl reduction, and Williamson ether synthesis. This three step synthesis includes all three of these classic reactions to make a symmetrical diether. A green route to this product was attainted by using toluene instead of the benzene in the first step. Since benzene is more toxic than toluene this is an appropriate green improvement. First 3-sulfolene was reacted with maleic anhydride to create endo cis-4-cyclohexane-1,2-dicarboxylic anhydride. This anhydride was then reduced using LiAlH₄ to create a diol which was then subjected to two rounds of Williamson Ether synthesis to create symmetrical ether.