Synthesis of 1-Hexyl-3-methylimidazolium Chloride; 1-Hexyl-3-methylimidazolium Chloride
Submitted Jul 06, 2015, published Jul 22, 2015
Jeraime Griffith (firstname.lastname@example.org
A contribution from
See Synthetic Page 747 for experimental setup.
A two-necked round bottomed flask containing 1-methylimidazole (37 mL, 464 mmol) and dry ethyl acetate (37 mL) under nitrogen was cooled in an ice bath. 1-chlorohexane (70 mL, 510 mol) was added dropwise, with stirring. Following complete addition, the ice bath was removed and the reaction mixture allowed to warm to room temperature before heating to 60 - 70°C for 11 days. After cooling to room temperature, and while still under nitrogen, the upper layer was decanted using a cannula. Excess 1-chlorohexane was removed from the lower viscous layer by washing with excess toluene. After removal of the solvent and drying at 50°C under high vacuum, the product was obtained as a clear colourless viscous oil (71.6%)
1HNMR (400 MHz, DMSO-d6) δH 9.38 (1H, s), 7.84 (1H, s), 7.77 (1H, s), 4.18 (2H, t), 3.87 (3H, s), 1.78 (2H, quintet), 1.30-1.21 (6H, m), 0.86 (3H, t).
13CNMR (101 MHz, DMSO-d6) δC 137.22, 124.03, 122.73, 49.12, 36.16, 31.03, 29.86, 25.61, 22.34, 14.28.
m/z 167 ([C6C1im]+, 100%), 83, 37, 35 (Cl-, 100%).
[C6C1im]Cl, H-NMR, DMSO-d6 (1-Hexyl-3-methylimidazolium Chloride, H-NMR, DMSO-d6.pdf)
[C6C1im]Cl, C-NMR, DMSO-d6 (1-Hexyl-3-methylimidazolium Chloride, C-NMR, DMSO-d6.pdf)
Photo, [C6C1im]Cl ([C6C1im]Cl.jpg)
Keywords: alkylation, amines, heterocyclic compounds, imidazolium, ionic liquid, liquid salts, nucleophilic, substitution