Phase Transfer Catalyzed Preparation of 4-Methylbenzenesulfonyl Imidazole for Regioselective Synthesis of Mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin

I Wayan Muderawan (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Ganesha University of Education, Singaraja 81117, Bali, Indonesia)
I Wayan Mudianta (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Ganesha University of Education, Singaraja 81117, Bali, Indonesia)
Made Kurnia Wiastuti Giri (Study Program of Medicine, Faculty of Medicine, Ganesha University of Education, Singaraja 81117, Bali, Indonesia)

Indonesian Journal of Chemistry
Vol 22, No 5 (2022)

The preparation of 4-methylbenzenesulfonyl imidazole by using triethylamine as an effective phase‐transfer catalyst (PTC) under mild biphasic conditions has been studied intensively. The method can be used for large-scale preparation with high purity and high yield of 4-methylbenzene-sulfonyl imidazole. The result in 4-methylbenzenesulfonyl imidazole has been successfully applied for the regioselective synthesis of mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin in an aqueous medium. This synthetic methodology concept, together with the synthetic versatility of PTC, provides a general and reliable general strategy for the practical and industrial regioselective synthesis of highly valuable mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin as a key intermediate for the single functional isomer mono-substituted cyclodextrin derivatives. As characterized by FTIR, NMR and mass spectrometry, mono-6-(4-methylbenzenesulfonyl)-β-cyclodextrin was obtained in high purity.