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Synthesis of Ethers by GaBr3-Catalyzed Reduction of Carboxylic Acid Esters and Lactones by Siloxanes

Authors

  • Dr. Ursula Biermann,

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    1. Institut für Chemie, Carl-von-Ossietzky-Universität Oldenburg, Carl-von-Ossietzky-Straße 9–11, 26111 Oldenburg (Germany)
    • Institut für Chemie, Carl-von-Ossietzky-Universität Oldenburg, Carl-von-Ossietzky-Straße 9–11, 26111 Oldenburg (Germany)

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  • Prof. Dr. Jürgen O. Metzger

    1. Institut für Chemie, Carl-von-Ossietzky-Universität Oldenburg, Carl-von-Ossietzky-Straße 9–11, 26111 Oldenburg (Germany)
    2. abiosus e.V. Bloherfelder Straße 239, 26129 Oldenburg (Germany)
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Abstract

Ethers were synthesized by reduction of the respective esters catalyzed by gallium bromide (GaBr3) and using siloxanes, preferentially 1,1,3,3-tetramethyldisiloxane, as reductant. Methyl oleate, triglycerides, that is, tributyrine and glyceryl triundec-10-enoate as well as γ- and δ-lactones were converted into the respective ethers in high to moderate yields. γ-Lactones were reduced with high selectivity in the presence of a methyl ester functionality. The reduction has been carried out at room temperature or moderately elevated temperature of up to 60 °C using stoichiometric amounts of the reductant and 0.005–0.01 equiv of GaBr3 as catalyst per ester functionality without any solvent added. After a reaction time of 1–4 h the conversion of the substrate was 100 %. The product was separated from polymeric siloxanes formed as coupled product by simple distillation.

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