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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ISSN2470-1343
2470-1343
DOI10.1021/acsomega.1c05159

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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.
AbstractList 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.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.
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.
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.
Author Wu, Yikang
An, Xiaosheng
Xu, Ze-Jun
Han, Wei-Bo
Zha, Qinghong
AuthorAffiliation State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis
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Snippet 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...
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...
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...
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Title A Low-Cost and Scalable Synthesis of a Cyclohexanone-Related Bifunctional Building Block
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