Reacción #2045022

Ecuación de reacción

2-(4-Isocyanato-phenoxy)-propionic acid methyl ester

ethylene glycol

→

33

Rendimiento 50.8%

2-[4-(2-Hydroxy-ethoxycarbonylamino)-phenoxy]-propionic acid methyl ester

Rendimiento 50.8%

Disolventes

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrorose to 58° C
2. 2
   Temperaturato cool
3. 3
   Extraccióncrude 33 was extracted into chloroform
4. 4
   Lavadowashed with water (2×50 ml)
5. 5
   Secadodried over sodium sulphate
6. 6
   workup.DISTILLATIONdistilled
7. 7
   OtroCrude 33 was purified by column chromatography on silica gel

Procedimiento

2-(4-Isocyanato-phenoxy)-propionic acid methyl ester 32 (20 g, 90.49 mmol) was added to ethylene glycol (40 ml) at room temperature. The reaction was exothermic and the temperature rose to 58° C. The mixture was allowed to cool and later stirred at room temperature for 16 hours. Water (150 ml) was added and crude 33 was extracted into chloroform, washed with water (2×50 ml), dried over sodium sulphate and distilled. Crude 33 was purified by column chromatography on silica gel using chloroform as eluant to get pure 33 (13 gr, 50.76%) as a syrup which crystallized in 48 hours as a white powder. M.p: 90.5-92.8° C.

Fuente