Acetone → HCID 22609181, compound

Participants

Reaction Steps

To a 100 mL flask containing diethanolamine (19.2 mL, 200 mmol) was added acetone (29.4 mL, 400 mmol, 2 eq.) and potassium carbonate (pulverised and dried at 160° C., 27.6 g, 200 mmol, 1 eq.). The reaction was stirred at room temperature for one day. The mixture was filtered through a sinter funnel (no. 3) and the collected solid was washed with acetone. The filtrate and the washes were combined and the solvent evaporated. The 1H NMR indicated a conversion of 85%. Distillation at 125-132° C./20 mmHg of the crude reaction gave the title product (20.89 g, 72% yield) as a colourless oil. 1H NMR (CDCl3, 400 MHz) d?(ppm): 3.93 (t, J=6.6 Hz, 2H); 3.62 (t, J=5.3 Hz, 2H); 2.96 (t, J=6.6 Hz, 2H); 2.65 (t, J=5.3 Hz, 2H); 1.23 (s, 6H). 13C NMR (CDCl3, 129.9 MHz) d??(ppm): 94.2; 63.5; 59.3; 50.8; 49.1; 23.3 (2C).

Provenance & Evidence