Flow Friedel–Crafts alkylation of 1-adamantanol with arenes using HO-SAS as an immobilized acid catalyst

Takayoshi Kasakado, Mamoru Hyodo, Akihiro Furuta, Aina Kamardine, Ilhyong Ryu*, Takahide Fukuyama

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Flow Friedel–Crafts alkylation was studied using hydroxy-substituted sulfonic acid-functionalized silica as a catalyst and 1-adamantanol as a model substrate. The reaction of 1-adamantanol (1a) with toluene (2a) proceeded well with 5 min of residence time at 120°C to give good yield of 1-tolyladamantane (3a) as a 1:9 mixture of meta and para isomers. When the flow synthesis was carried out over 2.5 hr of running time, the collected five fractions contain the product 3a in 97–92% yields, suggesting the durability of the catalyst.

    Original languageEnglish
    JournalJournal of the Chinese Chemical Society
    DOIs
    StateAccepted/In press - 2020

    Keywords

    • 1-aryladamantanes
    • flow Friedel–Crafts alkylation
    • hydroxy-substituted sulfonic acid-functionalized silica

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