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

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-m...

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Published inACS omega Vol. 6; no. 45; pp. 30811 - 30817
Main Authors Zha, Qinghong, An, Xiaosheng, Xu, Ze-Jun, Han, Wei-Bo, Wu, Yikang
Format Journal Article
LanguageEnglish
Published American Chemical Society 16.11.2021
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Summary: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.
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ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.1c05159