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Condensation of aromatic aldehydes with N,N-dimethylacetamide in presence of dialkyl carbonates as dehydrating agents

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Abstract

Reactions of benzaldehydes with excess N,N-dimethylacetamide at 140 °C in the presence of diethyl carbonate as dehydrating agent and a base gave (E)-N,N-dimethylcinnamamides in good yields. If hydroxybenzaldehydes are used as substrates the reaction is accompanied by alkylation.

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Acknowledgments

We are grateful to the Grant Agency of the Czech Republic, projects No. 203/07/P248, 104/09/0829 and Ministry of Education, Youth and Sports of the Czech Republic MSM 0021627501 and MSM 0021627502 for financial support.

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Authors and Affiliations

  1. Institute of Environmental and Chemical Engineering, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 53210, Pardubice, Czech Republic

    Tomáš Weidlich

  2. Department of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, 61137, Brno, Czech Republic

    Lubomír Prokeš

  3. Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 53210, Pardubice, Czech Republic

    Aleš Růžička & Zdeňka Padělková

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  1. Tomáš Weidlich
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  2. Lubomír Prokeš
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Correspondence to Tomáš Weidlich.

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Weidlich, T., Prokeš, L., Růžička, A. et al. Condensation of aromatic aldehydes with N,N-dimethylacetamide in presence of dialkyl carbonates as dehydrating agents. Monatsh Chem 141, 205–211 (2010). https://doi.org/10.1007/s00706-009-0248-x

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  • DOI: https://doi.org/10.1007/s00706-009-0248-x

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