Peracetic Acid → 4-(2,3-Epoxypropyl)-2,6-dichlorophenyl glycidyl ether
Reaction equation
[CH2:1]([O:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([CH2:13][CH:14]=[CH2:15])=[CH:8][C:7]=1[Cl:16])[CH:2]1[O:4][CH2:3]1.C(OO)(=[O:19])C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Na+]>[CH2:1]([O:5][C:6]1[C:7]([Cl:16])=[CH:8][C:9]([CH2:13][CH:14]2[O:19][CH2:15]2)=[CH:10][C:11]=1[Cl:12])[CH:2]1[O:4][CH2:3]1Participants
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.
Workup
- customequipped with stirrer
- additionAfter the dropwise addition
- customthe resultant aqueous phase is separated
- washthe organic phase is washed with two 150 ml portions of NaHCO3 (5%)
- washwashed with 150 ml of water
- dry with materialThe organic phase is dried over sodium sulfate
- filtrationfiltered
- concentrationThe filtrate is concentrated
Sources & evidence
- ORD record
- ord-652355d8c729482398cb6fea03dd1456
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04724031
Reaction notes
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