3-Chloro-1,2-propanediol → 1-(2,3-Dihydroxypropyl)-3-propylimidazolium Chloride

Participants

Reaction Steps

1-Propylimidazole (2.75 g, 25.0 mmol) and 3-chloro-1,2-propanediol (2.76 g, 25.0 mmol) were stirred in a 130° C. oil bath for 48 h, after which the flask was placed under vacuum and stirring continued at 130° C. for another 48 h. The residue was then dissolved in CH3OH, transferred to a tared flask and concentrated to afford the product as a viscous brown oil (5.20 g, 95%). 1H NMR: δH ppm (400 MHz; DMSO-d6) 0.84 (t, J=7.42 Hz, 3H) 1.74-1.86 (m, 2H) 3.22 (dd, J=11.17, 6.96 Hz, 1H) 3.42 (dd, J=10.99, 4.95 Hz, 1H) 4.07-4.20 (m, 3H) 4.33 (dd, J=13.74, 3.11 Hz, 1H) 5.15 (br. s., 1H) 5.56 (br. s., 1H) 7.78 (t, J=1.74 Hz, 1H) 7.82 (t, J=1.83 Hz, 1H) 9.29 (t, J=1.47 Hz, 1H).

Provenance & Evidence