Ethylene Glycol → HCID 15521920, compound

Participants

Reaction Steps

To a solution of 2-1 (38 g, 0.239 mol) in 500 mL benzene was added ethylene glycol (17.3 mL, 0.310 mol) and p-toluenesulfonic acid (1 g). The mixture was heated at reflux for 2 h with azeotropic removal of water. After cooling, the solution was washed with 200 mL sat. NaHCO3, brine, and dried over Na2SO4. Evaporative removal of the solvent gave 2-2 as a yellow oil. TLC Rf =0.62 (silica, ethyl acetate). 1H NMR (300 MHz, CDCl3) δ 3.95 (m, 4H), 3.68 (s, 3H), 3.17 (s, 3H), 2.51 (t, 2H, J=8 Hz), 2.00 (t, 3H, J=6 Hz) 1.33 (S, 3H).

Provenance & Evidence