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

9 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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