Réaction #5340

Équation de réaction

phenyl glycidyl ether

oxirane

p-toluenesulfonic acid monohydrate

phenothiazine

→

3-Phenoxy-1,2-propanediol

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 6.0 hours
2. 2
   TempératureUpon cooling
3. 3
   workup.ADDITIONthe reactor was charged with 186.0 g
4. 4
   TempératureThe mixture was again heated
5. 5
   Températureat reflux
6. 6
   ExtractionThe product was extracted with ether
7. 7
   Autrepurified
8. 8
   Lavageby washing
9. 9
   Autreat 25° C.

Mode opératoire

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.

Source