Synthesis of 7-Alkoxy-4-trifluoromethylcoumarins via the Pechmann Condensation Reaction Using Catalytic Iodine

Jami DeGrote

Abstract


Coumarin derivatives are common compounds used widely in the scientific community, ranging from pharmaceutical to commercial applications. 7-Alkoxy-4-trifluoromethylcoumarins are used in fluorometric enzyme assays and to make laser dyes. Due to the fact that these coumarin derivatives are relatively expensive to purchase and are found in small quantities, it is advantageous to synthesize these compounds both cost effectively and in larger quantities. This paper reports the synthesis of several 7-alkoxy-4-trifluoromethylcoumarins via the Pechmann condensation reaction using molecular iodine as a catalyst. 7-Hydroxy-4-trifluoromethylcoumarin, 7-methoxy-4-trifluoromethylcoumarin, 7-ethoxy-4-trifluoromethylcoumarin, and 7-benzyloxy-4-trifluoromethylcoumarin have been successfully synthesized (71%, 37%, 41%, 24%, respectively). All coumarin derivatives were purified through flash chromatography and confirmed by NMR spectroscopy.


Keywords


Coumarin; Pechmann Condensation

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