Flow Friedel–Crafts alkylation of 1‐adamantanol with arenes using HO‐SAS as an immobilized acid catalyst. Issue 12 (11th December 2020)

• Record Type: Journal Article
• Authors: Kasakado, Takayoshi; Hyodo, Mamoru; Furuta, Akihiro; Kamardine, Aina; Ryu, Ilhyong; Fukuyama, Takahide
• Is Part Of: Journal of the Chinese Chemical Society. Volume 67:Issue 12(2020)
• Page Start: 2253
• Page End: 2257
• Publication Date: 2020-12-11
• Subjects: 1‐aryladamantanes -- flow Friedel–Crafts alkylation -- hydroxy‐substituted sulfonic acid‐functionalized silica; Chemistry -- Periodicals; Electronic journals; 540.5
• DOI: 10.1002/jccs.202000518
• Languages: English
• ISSNs: 0009-4536

Abstract

Abstract: 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. Abstract : 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.