Reacción #1166469

Ecuación de reacción

N-(2-hydroxyethoxyethyl)hexahydrophthalimide

triethylamine

acryloyl chloride

→

orange-red liquid

Rendimiento 59.5%

N-(Acryloyloxyethoxyethyl)hexahydrophthalimide

Rendimiento 59.5%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA one liter, three necked flask was equipped with overhead stirrer
2. 2
   OtroThe triethylamine hydrochloride salt was removed by filtration
3. 3
   Otrothe remaining mother liquor was evaporated with a rotoevaporator
4. 4
   workup.DISSOLUTIONThe resulting red-orange liquid was dissolved in chloroform
5. 5
   Extracciónextracted with HCl(10%), NaCl(aq.), NH4OH(10%), NaCl(aq.)
6. 6
   Secadodried over MgSO4
7. 7
   OtroThe chloroform was removed with a rotoevaporator

Procedimiento

A one liter, three necked flask was equipped with overhead stirrer, nitrogen atmosphere and an addition funnel. The flask was charged with 100 g of N-(2-hydroxyethoxyethyl)hexahydrophthalimide (0.41 mol.), 42 g of triethylamine (0.41 mol.), 1 g of phenothiazine and 400 ml of acetone. Next, 38 g of acryloyl chloride (0.41 mol.) was added slowly to the flask via the addition funnel over 45 minutes. The reaction was stirred for an additional 12 hours. The triethylamine hydrochloride salt was removed by filtration and the remaining mother liquor was evaporated with a rotoevaporator. The resulting red-orange liquid was dissolved in chloroform and extracted with HCl(10%), NaCl(aq.), NH4OH(10%), NaCl(aq.) and dried over MgSO4. The chloroform was removed with a rotoevaporator to yield 72 g (59%) of an orange-red liquid. The product was confirmed by IR and 13C NMR.

Fuente