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Flow Friedel–Crafts alkylation of 1‐adamantanol with arenes using HO‐SAS as an immobilized acid catalyst
Author(s) -
Kasakado Takayoshi,
Hyodo Mamoru,
Furuta Akihiro,
Kamardine Aina,
Ryu Ilhyong,
Fukuyama Takahide
Publication year - 2020
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.202000518
Subject(s) - chemistry , friedel–crafts reaction , catalysis , alkylation , toluene , substrate (aquarium) , yield (engineering) , sulfonic acid , organic chemistry , medicinal chemistry , oceanography , materials science , metallurgy , geology
In this communication 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.