Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste-Free Synthesis of Pristane

Akihiro Furuta, Yuki Hirobe, Takahide Fukuyama*, Ilhyong Ryu, Yoshiyuki Manabe, Koichi Fukase

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    10 Scopus citations

    Abstract

    Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) in combination with THF containing a small amount of water as a solvent proved to be a reliable system for the dehydration of allylic alcohols. This process generally caused dehydration within 1 min through a column reactor charged with HO-SAS. The flow dehydration was sequenced by flow hydrogenation, which resulted in the synthesis of pristane. A scalable flow synthesis of pristane was successfully performed and afforded 10 g of pristane after an operation of 2 h. We also performed dehydration and hydrogenation by using a mixed column of HO-SAS and 10 % Pd/C.

    Original languageEnglish
    Pages (from-to)1365-1368
    Number of pages4
    JournalEuropean Journal of Organic Chemistry
    Volume2017
    Issue number10
    DOIs
    StatePublished - 10 Mar 2017

    Keywords

    • Allylic compounds
    • Dehydration
    • Hydrogenation
    • Microreactors
    • Solid acids

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