Journal of Siberian Federal University. Chemistry / Reaction of Esters with Thionyl Chloride Catalyzed by Zinc Halides

Full text (.pdf)
Issue
Journal of Siberian Federal University. Chemistry. 2024 17 (3)
Authors
Boyandin, Anatoly N.; Tyulkina, Eugenia N.; Sukhanova, Anna A.; Ertiletskaya, Natalya L.
Contact information
Boyandin, Anatoly N.: Reshetnev Siberian State University of Science and Technology; Institute of Biophysics SB RAS FRC “Krasnoyarsk Science Center of the SB RAS” Krasnoyarsk, Russian Federation; ; Tyulkina, Eugenia N.: Reshetnev Siberian State University of Science and Technology Krasnoyarsk, Russian Federation; Sukhanova, Anna A.: Reshetnev Siberian State University of Science and Technology Krasnoyarsk, Russian Federation; Ertiletskaya, Natalya L.: Reshetnev Siberian State University of Science and Technology ” Krasnoyarsk, Russian Federation
Keywords
esters; thionyl chloride; haloalkanes; zinc; catalyst
Abstract

The ability of esters of primary and secondary alcohols butyl acetate and L‑menthyl acetate (2-isopropyl‑5-methylcyclohexyl acetate) to interact with thionyl chloride in the presence of zinc halides (chloride or bromide) was studied. 1-chlorobutane with a minor admixture of 2-chlorobutane (less than 3.6 %) was the main product of the reactions of butyl acetate. For L‑menthyl acetate, the main product was 2-chloro‑1-isopropyl‑4-methylcyclohexane with minor impurities mainly represented by 1-isopropyl‑4-methylcyclohexene and other six-membered unsaturated hydrocarbons. When ZnBr2 used as a catalyst, impurities of bromo- substituted hydrocarbons were found in the reaction products, which demonstrates the possibility of halogen atoms exchange between zinc halide and the resulting organic products of the reaction

Pages
482–490
EDN
YMMNEV
Paper at repository of SibFU
https://elib.sfu-kras.ru/handle/2311/153824