Reacción #5340

Ecuación de reacción

phenyl glycidyl ether

oxirane

p-toluenesulfonic acid monohydrate

phenothiazine

→

3-Phenoxy-1,2-propanediol

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 6.0 hours
2. 2
   TemperaturaUpon cooling
3. 3
   workup.ADDITIONthe reactor was charged with 186.0 g
4. 4
   TemperaturaThe mixture was again heated
5. 5
   Temperaturaat reflux
6. 6
   ExtracciónThe product was extracted with ether
7. 7
   Otropurified
8. 8
   Lavadoby washing
9. 9
   Otroat 25° C.

Procedimiento

A solution of 150.2 g. phenyl glycidyl ether (1.0 eq.), 200.0 g. AOnPA (1.15 eq., of Example 1), 200.0 g. toluene, 4.0 g. tetrapropylammonium bromide (0.015 eq.), and 1.0 g. phenothiazine was heated at reflux for 6.0 hours. Conversion, measured by residual oxirane titer, was ca. 93%. Upon cooling, the reactor was charged with 186.0 g. of the AOnPA (1.07 eq.), 150.0 g. toluene, and 10.0 g. p-toluenesulfonic acid monohydrate (0.05 eq.). The mixture was again heated at reflux. After 6.0 hrs., conversion was 90%. The product was extracted with ether and purified by washing. It had an acrylate titer of 3.8 meq./g. (theory: 4.17 meq./g.) and Brookfield viscosity of 230 centipoise at 25° C.

Fuente