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The synergistic effect of copper chromite spinel nanoparticles (CuCr2O4) and basic ionic liquid on the synthesis of cyclopropanecarboxylic acids

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Abstract

An efficient synthesis of cyclopropanecarboxylic acids using copper chromite spinel nanoparticles and basic ionic liquid is described. In this study, a relatively simple method starting with trans-cinnamic acid for the synthesis of (±)-trans-2-phenylcyclopropanecarboxylic acid, a key intermediate in the synthesis of tranylcypromine sulfate as an active pharmaceutical ingredient, was employed. Using a combination of basic ionic liquid [Bmim]OH and copper chromite spinel nanoparticles as a catalytic system, the best results were obtained in THF as a polar solvent. This method is a useful alternative to other approaches described in the literature. The use of commercially available chemicals, decreased environmental hazards, with no need for the separation of stereoisomers, and consequently a reduced number of overall steps, are the advantages of this approach that make it an appropriate choice at an increased scale.

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Acknowledgments

The authors wish to gratefully thank the Research Affairs Division at Amir Kabir University of Technology (AUT), Tehran, for financial support and the TEMAD Pharmaceutical Co. for financial supports.

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Authors and Affiliations

  1. Department of Chemistry, Amirkabir University of Technology, Hafez Avenue, No. 424, P.O. Box: 159163-4413, Tehran, Iran

    Mohammad Hadi Ghasemi & Elaheh Kowsari

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  1. Mohammad Hadi Ghasemi
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  2. Elaheh Kowsari
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Correspondence to Elaheh Kowsari.

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11164_2016_2572_MOESM1_ESM.pdf

Supporting information (experimental procedures, catalyst characterization, 1H NMR, 13C NMR and FTIR spectra) related with this article can be found in the supplementary material (PDF 1790 kb)

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Ghasemi, M.H., Kowsari, E. The synergistic effect of copper chromite spinel nanoparticles (CuCr2O4) and basic ionic liquid on the synthesis of cyclopropanecarboxylic acids. Res Chem Intermed 42, 7963–7975 (2016). https://doi.org/10.1007/s11164-016-2572-1

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  • DOI: https://doi.org/10.1007/s11164-016-2572-1

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