A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block

Abstract

A practical route to 2-(2-(2-methyl-1,3-dioxolan-2-yl)­ethyl)­cyclohexan-1-one was developed, featuring the use of inexpensive starting materials/reagents and readily attainable reaction conditions. The overall transformation was achieved in 53% yield with one chromatographic purification via NaOH-mediated aldol condensation, ethylene glycol protection of the ketone group in the presence of HC­(OEt)3/concd HCl, saturation of the CC bond and the benzene ring with Al–Ni alloy in aqueous KOH, and oxidation of the intermediate cyclohexanol with aqueous NaClO/TEMPO/KBr.