Reacción #1166467

Ecuación de reacción

2-hydroxyethylacrylate

triethylamine

phthaloyl chloride

→

desired product

Rendimiento 100.4%

Di(acryloyloxyethyl)phthalate

Rendimiento 100.4%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA five liter, three necked flask was equipped with a overhead stirrer
2. 2
   workup.ADDITIONnitrogen atmosphere and addition funnel
3. 3
   OtroThe triethylamine hydrochloride salt was removed by filtration
4. 4
   Otrothe mother liquor evaporated by rotoevaporation
5. 5
   Otroto yield an amber colored liquid
6. 6
   Temperaturaheated to 100° C. for one hour
7. 7
   OtroThe resulting liquid was collected

Procedimiento

A five liter, three necked flask was equipped with a overhead stirrer, nitrogen atmosphere and addition funnel. The flask was charged with 636 g of 2-hydroxyethylacrylate (5.47 mol.), 547 g of triethylamine (5.41 mol.), 6 g of phenothiazine, 5 g of 4-dimethylaminopyridine and 3000 ml of tetrahydrofuran. The reaction was cooled to 17° C. with a water bath. Next, 563 g of phthaloyl chloride (2.75 mol.) was slowly added over 2.5 hours via the addition funnel. The reaction was stirred an additional 8 hours at room temperature. The triethylamine hydrochloride salt was removed by filtration and the mother liquor evaporated by rotoevaporation to yield an amber colored liquid. The liquid was placed under vacuum (15 mmHg, 2 kPa) and heated to 100° C. for one hour. The resulting liquid was collected to yield 995 g (99%) of the desired product. The product was confirmed by IR and 13C NMR. The preparation of di(acryloyloxyethyl)phthalate from phthalic anhydride and 2-hydroxyethylacrylate was reported in U.S. Pat. No. 3,336,418.

Fuente