Reaction #5340

Reaction equation

phenyl glycidyl ether

oxirane

p-toluenesulfonic acid monohydrate

phenothiazine

→

3-Phenoxy-1,2-propanediol

Solvents

toluene

toluene

Conditions

Workup

1. 1
   Temperatureat reflux for 6.0 hours
2. 2
   TemperatureUpon cooling
3. 3
   workup.ADDITIONthe reactor was charged with 186.0 g
4. 4
   TemperatureThe mixture was again heated
5. 5
   Temperatureat reflux
6. 6
   ExtractionThe product was extracted with ether
7. 7
   Otherpurified
8. 8
   Washby washing
9. 9
   Otherat 25° C.

Procedure

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