Reacción #2267061

Ecuación de reacción

ethylene glycol vinyl ether

epibromohydrin

Sodium hydroxide

→

2-vinyloxyethylglycidyl ether

Rendimiento 60.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 1000 ml three-necked round bottom flask, equipped with a thermocouple, magnetic stirrer
2. 2
   Temperaturaheating mantle
3. 3
   workup.ADDITIONwere then added portionwise, with the reaction temperature
4. 4
   FiltraciónThe mixture was then filtered
5. 5
   Lavadorinsed with a small amount of toluene
6. 6
   OtroThe toluene was removed
7. 7
   Otroa rotary evaporator under reduced pressure
8. 8
   workup.DISTILLATIONthe crude product distilled under vacuum

Procedimiento

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).

Fuente