1-Methylimidazole → (E)-1-(2-(3,7-dimethylocta-2,6-dienyloxy)-2-oxoethyl)-3-methyl-1H-imidazol-3-ium chloride

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Reaction Conditions

Reaction Steps

Geraniol ester [2] (2.307 g, 10 mmol) and N-methylimidazole (0.821 g, 10 mmol) were mixed in and stirred in a sealed vessel at 40° C. for 24 hrs. A light-brown solid was formed and suspended in anhydrous diethylether. The solid precipitate was filtered, washed with diethylether and dried under reduced pressure (0.01 mbar) to give imidazolium chloride [3] in 67% yield as light-yellow hygroscopic solid. The product was pure according to 1H NMR and directly subjected to the next step without further purification. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=9.36 (s, 1H), 7.82 (s, 2H), 5.37 (s, 2H), 5.33 (t, J=7.0 Hz, 1H), 5.07 (s, 1H), 4.68 (d, J=7.1 Hz, 2H), 3.93 (s, 3H), 2.03 (m, 4H), 1.66 (s, 3H), 1.64 (s, 3H), 1.56 (s, 3H). 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=166.9, 142.6, 137.8, 131.1, 123.7, 123.6, 123.3, 117.8, 62.4, 49.4, 35.9, 25.8, 25.5, 17.6, 16.1. mp 160° C. (dec), T5%onset 125° C.

Provenance & Evidence