Flow Chemistry under Extreme Conditions: Synthesis of Macrocycles with Musklike Olfactoric Properties

J Org Chem. 2021 Oct 15;86(20):13924-13933. doi: 10.1021/acs.joc.1c00663. Epub 2021 Apr 26.

Abstract

Starting from small cyclic ketones, continuous flow synthesis is used to produce medium-sized rings and macrocycles that are relevant for the fragrance industry. Triperoxides are important intermediates in this process and are pyrolyzed at temperatures above 250 °C. The synthesis is carried out in two continuously operated flow reactors connected by a membrane-operated separator. The practicality of flow chemistry is impressively demonstrated in this work by the use of hazardous reagent mixtures (30% H2O2, 65% HNO3) and the pyrolysis of no less problematic peroxides. All new macrocycles were tested for their olfactory properties in relation to musk.

MeSH terms

  • Hydrogen Peroxide*
  • Indicators and Reagents
  • Ketones*
  • Physical Phenomena

Substances

  • Indicators and Reagents
  • Ketones
  • Hydrogen Peroxide