Synthesis of carbonyl compounds dibenzo-18- crown-6 by the Grinard reaction

Abstract

In this article, Grignard reactions of 4´,4´´-diiododibenzo-18- crown-6 were carried out to obtain carbonyl compounds in an inert argon atmosphere. An aldehyde, 4´,4´´-diformyldiioddibenzo-18-crown-6, and a ketone, 4´,4´´-diacetyldibenzo-18-crown-6, were obtained. The reactivity and geometry of ethyl acetate, acetic anhydride, and acetic acid chloride molecules were analyzed, which was reflected in the difference in the yields of the target product: ester (22%) <anhydride (37%) <acid chloride (48%). It was determined that tertiary alcohols and various oxidation products are by-products of the reaction. A quantum-chemical calculation and comparison of the spectra of carbonyl compounds, diacetyldibenzo-18- crown-6 were performed. The obtained compounds were identified using 1H-13C-NMR and IR spectroscopy.