Synthesis of Citronellol from Isoprene

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  • HIDAI Masanobu
    Department of Industrial Chemistry, Fuculty of Engineering, University of Tokyo
  • YAGI Hiroshi
    Department of Industrial Chemistry, Fuculty of Engineering, University of Tokyo
  • TANAKA Eisuke
    Department of Industrial Chemistry, Fuculty of Engineering, University of Tokyo
  • ISHIWATARI Hisayasu
    Department of Industrial Chemistry, Fuculty of Engineering, University of Tokyo
  • UCHIDA Yasuzo
    Department of Industrial Chemistry, Fuculty of Engineering, University of Tokyo

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Other Title
  • イソプレンの二量化によるシトロネロールの合成
  • イソプレン ノ ニリョウカ ニヨル シトロネロール ノ ゴウセイ

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Many natural terpenic compounds are known to have skeltons of 1-4 addition of isoprene. But few terpenic compounds have been synthesized hitherto. <BR>We shall now report the synthesis of citronellol VII-a natural monoterpene alcohol-from isoprene. <BR>The reaction consists of the f olloouing four steps ; <BR>(1) Catalytic dimerization and alcohol addition of isoprene in the presence of (π-allyl PdCI) 2, phos-phine, and NaOMe. <BR>The yield of II is up to 97.5% when PPh3 : (π-allyl PdCI) 2=2 : 1 and 2 days reaction at room temperature. <BR>(2) Dealcohol reaction of If or V is carried out in the presence of [P (η-Bu) 3] 2 NiCl2 and NaOMe as catalytic system, <BR>(3) Selective 1-4 hydrogenation of conjugated diene is carried out in the presence of Cr (CO) 3 (C6H, -COOMe) as a catalyst under hydrogen atmosphere to form IV or VI. <BR>(4) Terminal hydration of terminal double bond is carried out by hydroboration and following alkaline hydrolysis to obtain V or VII.<BR>Two synthetic routes are practically possible and the overall yield of citronellol is ca. 40% in each case.

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