Flow Friedel–Craftsalkylation of 1‐adamantanolwith arenes using HO‐SASas an immobilized acid catalyst

Autor: Kasakado, Takayoshi, Hyodo, Mamoru, Furuta, Akihiro, Kamardine, Aina, Ryu, Ilhyong, Fukuyama, Takahide
Zdroj: Journal of the Chinese Chemical Society; December 2020, Vol. 67 Issue: 12 p2253-2257, 5p
Abstrakt: 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 metaand paraisomers. When the flow synthesis was carried out over 2.5 hr of running time, the collected five fractions contain the product 3ain 97–92% yields, suggesting the durability of the catalyst. Flow Friedel–Crafts alkylation was studied using 1‐adamantanol as alkylating reagent and hydroxy‐substituted sulfonic acid‐functionalized silica (HO‐SAS) as a catalyst. The flow reaction proceeded with typical aromatic compounds to give the corresponding alkylated products in good yields. Running the reaction of 1‐adamantanol with toluene over 2.5 h did not cause a significant decrease of the product yield.
Databáze: Supplemental Index