Expedient synthesis of (E)‐3‐methylcyclopentadec‐2‐en‐1‐one, an important precursor for (R)‐(−)muscones

• Published in: Flavour and fragrance journal Vol. 27; no. 1; pp. 54 - 59
• Main Authors: Hagiwara, Hisahiro, Adachi, Teppei, Doya, Masaharu, Hoshi, Takashi, Suzuki, Toshio
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 2012; Wiley
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; condensation; Exact sciences and technology; hydrochloric acid; intramolecular aldol condensation; isomerization; muscone; olefin isomerization; Organic chemistry; Preparations and properties; vapour-phase reaction; zinc oxide; zinc oxide catalysis; Intramolecular reaction; Catalytic reaction; zinc oxide catalysis; Isomerization; Zinc Oxides; Precursor; Aldol condensation; intramolecular aldol condensation; Cyclization; Vapor phase; Trans stereoisomer; olefin isomerization; Chemical synthesis; vapour-phase reaction; Monocyclic compound; Ethylenic compound; muscone
• ISSN: 0882-5734; 1099-1026
• DOI: 10.1002/ffj.2080

An expedient synthesis of (E)‐3‐methylcyclopentadec‐2‐en‐1‐one, an important precursor for (R)‐(−)‐muscone, was developed. The key steps were vapour‐phase intramolecular aldol condensation catalysed by zinc oxide at 360 °C followed by double bond isomerization by the addition–elimination of hydrogen chloride.