New symmetrical imidazolium chloride from a natural chiral pool of (1R,2S,5R)-(-)-menthol can be efficiently prepared by two different methods. The first method involves a specific type of Menschutkin reaction using novel 1-(1R,2S,5R)-(-)-menthoxymethylimidazole as amine, chloromethyl (1R,2S,5R)-(-)-menthyl ether as quaternization agent, and hexane as solvent. In the second method, imidazole, chloromethyl (1R,2S,5R)-(-)-menthyl ether, and DMF are used. To understand this specific type of the reaction, quantum chemical calculations at the DFT level have been used. The preparation and characterization of 1,3-bis[(1R,2S,5R)-(-)-menthoxymethyl]imidazolium chloride are reported.
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