Hydroxyethyl vinyl ether → 2-{[2-(Ethenyloxy)ethoxy]methyl}oxirane

Participants

Reaction Conditions

Reaction Steps

To a 1000 ml three-necked round bottom flask, equipped with a thermocouple, magnetic stirrer and heating mantle, was added ethylene glycol vinyl ether (35.2 g; 0.400 moles), epibromohydrin (62.4 g; 0.456 mole), toluene (200 ml), and tetrabutylammonium bromide (1.5 g). Sodium hydroxide pellets (32 g 0.8 moles) were then added portionwise, with the reaction temperature maintained at 80° C. The reaction mixture was vigorously stirred for a period of time of about 1 hour at a temperature of 80° C. The mixture was then filtered and rinsed with a small amount of toluene. The toluene was removed using a rotary evaporator under reduced pressure and the crude product distilled under vacuum to yield 2-vinyloxyethylglycidyl ether (“VEGE”) (34.6 g; 60% yield), b.p. 55-57° C. at 0.75 torr. The structure of VEGE was confirmed by 1H NMR analysis (300 MHz; CDCl3): δ 6.5 (q, 1H, CH2═CH—), δ 4.0 and 4.2 (two d, 2H, CH2═CH—), δ 3.85 (m, 4H, O—CH2—CH2—O), δ 3.8 and 3.45 (m, 2H, O—CH2—CH—), δ 3.2 (m, 1H, epoxide ring —CH(CH2)—O), δ 2.6 and 2.8 (m, 2H, epoxide ring —CH(CH2)—O).

Provenance & Evidence