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

[Image: see text] 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 purific...

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Autores principales: Zha, Qinghong, An, Xiaosheng, Xu, Ze-Jun, Han, Wei-Bo, Wu, Yikang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8600635/
https://www.ncbi.nlm.nih.gov/pubmed/34805709
http://dx.doi.org/10.1021/acsomega.1c05159
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author Zha, Qinghong
An, Xiaosheng
Xu, Ze-Jun
Han, Wei-Bo
Wu, Yikang
author_facet Zha, Qinghong
An, Xiaosheng
Xu, Ze-Jun
Han, Wei-Bo
Wu, Yikang
author_sort Zha, Qinghong
collection PubMed
description [Image: see text] 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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spelling pubmed-86006352021-11-19 A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block Zha, Qinghong An, Xiaosheng Xu, Ze-Jun Han, Wei-Bo Wu, Yikang ACS Omega [Image: see text] 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. American Chemical Society 2021-11-02 /pmc/articles/PMC8600635/ /pubmed/34805709 http://dx.doi.org/10.1021/acsomega.1c05159 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Zha, Qinghong
An, Xiaosheng
Xu, Ze-Jun
Han, Wei-Bo
Wu, Yikang
A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block
title A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block
title_full A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block
title_fullStr A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block
title_full_unstemmed A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block
title_short A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block
title_sort low-cost and scalable synthesis of a cyclohexanone-related bifunctional building block
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8600635/
https://www.ncbi.nlm.nih.gov/pubmed/34805709
http://dx.doi.org/10.1021/acsomega.1c05159
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