Reaction #4244

Reaction equation

4-allyl-2,6-dichlorophenyl glycidyl ether

peracetic acid

→

pale yellow resin

Yield 92.3%

4-(2,3-Epoxypropyl)-2,6-dichlorophenyl glycidyl ether

Yield 92.3%

Solvents

toluene

sodium acetate

toluene

Conditions

Workup

1. 1
   Otherequipped with stirrer
2. 2
   workup.ADDITIONAfter the dropwise addition
3. 3
   Otherthe resultant aqueous phase is separated
4. 4
   Washthe organic phase is washed with two 150 ml portions of NaHCO3 (5%)
5. 5
   Washwashed with 150 ml of water
6. 6
   DryingThe organic phase is dried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   ConcentrationThe filtrate is concentrated

Procedure

A 100 ml sulfurating flask equipped with stirrer, cooler, thermometer and drip funnel is charged with 13.0 g (0.05 mole) of 4-allyl-2,6-dichlorophenyl glycidyl ether in 40 ml of toluene and 0.5 g of sodium acetate. Over 2 hours, 14.0 g (0.07 mole) of 10% peracetic acid are then added dropwise at 30°-50° C. After the dropwise addition, the reaction mixture is diluted with 300 ml of toluene, the resultant aqueous phase is separated and the organic phase is washed with two 150 ml portions of NaHCO3 (5%) and then washed with 150 ml of water. The organic phase is dried over sodium sulfate and made peroxide-free with sodium sulfite and filtered. The filtrate is concentrated, affording 12.7 g (92.3%) of a pale yellow resin with an epoxide content of 5.62 eq/kg (77.75%) and a viscosity of 280 mPas/25° C.

Source