تفاعل #5340

معادلة التفاعل

phenyl glycidyl ether

oxirane

p-toluenesulfonic acid monohydrate

phenothiazine

→

3-Phenoxy-1,2-propanediol

المذيبات

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 6.0 hours
2. 2
   درجة الحرارةUpon cooling
3. 3
   workup.ADDITIONthe reactor was charged with 186.0 g
4. 4
   درجة الحرارةThe mixture was again heated
5. 5
   درجة الحرارةat reflux
6. 6
   استخلاصThe product was extracted with ether
7. 7
   أخرىpurified
8. 8
   غسيلby washing
9. 9
   أخرىat 25° C.

الإجراء التجريبي

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.

المصدر