Novel Ether Synthesis in Ionic Liquids

April 4, 2022

Currently, the most useful synthetic tool for ether synthesis is the Williamson Ether Synthesis Method. However, the limitation of this method is that only primary or methyl groups can be used, which limits you to the creation of small Ethers. The Purpose of this project is to develop a new method for synthesizing bulky Ethers and Amines using novel ionic liquid solvents. In alcohol: ionic liquid dual solvent systems, solvolysis of 1-adamantyl mesylate forms a carbocation through a Kc reaction mechanism. The stabilizing effects of the ionic liquid solvent allows the carbocation to be primed for nucleophilic attack.  The subsequent carbocation is trapped by the alcohol cosolvent, thus forming an Ether.  The advantage of this method is that the solvent is not a competing factor for nucleophilic attack because Ionic Liquids are completely non-reactive as solvents. This means that a single product is guaranteed. Since proof of concept, the purpose has been to optimize reaction conditions and product yield so that this method can be seen as a useful tool for synthesizing naturally occurring and complex versions of these molecules. Various steps toward optimization have been made including reaction temperature, reaction time, concentration of starting materials, and purification methods. Multiple ethers have been successfully synthesized using this technique.

Copyright © 2022  Black Doctoral Network | All Rights Reserved
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram