Ethylene Glycol → 2-((3-Methyloxetan-3-yl)methoxy)ethanol

Participants

Reaction Conditions

Reaction Steps

Ethylene glycol (26.25 g, 0.42 mol) and KOH (19.45 g, 0.35 mol) were added to a round-bottom flask equipped with a magnetic stirrer and a reflux condenser. When all KOH had dissolved the 3-bromomethyl-3-methyloxetane (4) (46.30 g, 0.28 mol) was added. The system was heated to 70° C. for 3 hours. The reaction material was then distilled under vacuum (10 Torr) and collected as a single fraction. The distilled material was then extracted with diethyl ether and water. The water fraction was then extracted with CHCl3 multiple times to obtain 11.98 g (29.2% yield) of the final product, though analysis of the water phase indicated a significant amount of HE 1Ox was unextracted. H1 NMR (CDCl3): δ 1.31 ppm (—CH3, 3H, s), δ 2.63 ppm (—OH, 1H, t), δ 3.54 ppm (—CH2—, 2H, s), δ 3.60 ppm (—OCH2—, 2H, t), δ 3.76 ppm (HOCH2—, 2H, q), δ 4.38 ppm (oxetane CH2, 2H, d), δ 4.55 ppm (oxetane CH2, 2H, d).

Provenance & Evidence