Synthesis of a Renewable Macrocyclic Musk: Evaluation of Batch, Microwave, and Continuous Flow Strategies

    • Émilie Morin §
    • Johann Sosoe §
    • Michaël Raymond §
    • Benjamin Amorelli †*
    • Richard M. Boden
    • Shawn K. Collins
    • § Department of Chemistry and Centre for Green Chemistry and Catalysis, Université de Montréal, CP 6128 Station Downtown, Montréal, Québec, Canada H3C 3J7
    • Research & Development, International Flavors & Fragrances Inc., 1515 State Route 36, Union Beach, New Jersey, 07735, United States

    The renewable macrocyclic musk 3-methylcyclohexadec-6-enone was prepared via macrocyclic olefin metathesis on gram scale using two different protocols: a room temperature batch process which afforded a 57% yield of the desired macrocycle, but required long reaction times (5 d). In contrast, a continuous flow strategy provided a lower yield of 32% of macrocycle, although the short reaction times (150 °C, 5 min) improve throughput (1 g/4.8 h). Batch and continuous flow protocols were also tested on other macrocyclizations involving substrates bearing trisubstituted olefins.

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