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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.

SUBMITTER: Zha Q

PROVIDER: S-EPMC8600635 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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

Zha Qinghong Q An Xiaosheng X Xu Ze-Jun ZJ Han Wei-Bo WB Wu Yikang Y

ACS omega 20211102 45

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)<sub>3</sub>/concd HCl, saturation of the C=C bond and the benzene ring with Al-Ni alloy in aqueous K ...[more]

PMID: 34805709

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