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

Participants

Reaction Steps

1-Butylimidazole (12.42 g, 100.0 mmol) and 3-chloro-1,2-propanediol (11.05 g, 100.0 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 (23.27 g, 92%). 1H NMR: δH ppm (400 MHz; DMSO-d6) 0.89 (t, 3H) 1.17-1.31 (m, 2H) 1.69-1.83 (m, 2H) 3.19-3.28 (m, 1H) 3.37-3.46 (m, 1H) 3.78 (dd, J=7.05, 4.49 Hz, 1H) 4.12 (dd, J=13.83, 7.60 Hz, 1H) 4.20 (t, J=7.14 Hz, 2H) 4.33 (dd, J=13.74, 3.11 Hz, 1H) 5.16 (br. s., 1H) 5.56 (d, J=5.31 Hz, 1H) 7.78 (t, J=1.74 Hz, 1H) 7.83 (t, J=1.74 Hz, 1H) 9.30 (t, J=1.47 Hz, 1H).

Provenance & Evidence