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

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

ACS Omega

State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Published: November 2021

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)/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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8600635PMC
http://dx.doi.org/10.1021/acsomega.1c05159DOI Listing

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