Peracetic Acid → 4-(2,3-Epoxypropyl)-2,6-dimethylphenyl glycidyl ether
Reaction equation
[CH2:1]([O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH2:13][CH:14]=[CH2:15])=[CH:8][C:7]=1[CH3:16])[CH:2]1[O:4][CH2:3]1.C([O-])(=[O:19])C.[Na+].C(OO)(=O)C>C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[C:7]([CH3:16])=[CH:8][C:9]([CH2:13][CH:14]2[O:19][CH2:15]2)=[CH:10][C:11]=1[CH3:12])[CH:2]1[O:4][CH2:3]1Participants
Procedure
A 350 ml sulfurating flask equipped with thermometer, stirrer, cooler and drip funnel is charged with 46.30 g (0.21 mole) of 4-allyl-2,6-dimethylphenyl glycidyl ether, 1.93 g of sodium acetate and 160 ml of chloroform, and the batch is heated to 35°-40° C. At this temperature, 52.3 g (0.28 mole) of 40% peracetic acid are then added dropwise over about 1 hour. The reaction mixture is then held at this temperature for a further 4 hours until the educt is no longer discernible in the gas chromatograph. When the reaction is complete, the reaction mixture is diluted in chloroform and the resultant solution is washed with 3% NaOH until neutral, made peroxide-free with sodium sulfite, dried over sodium sulfate and filtered. The filtrate is concentrated by rotary evaporation, affording 47.6 g of 4-(2,3-epoxypropyl)-2,6-dimethylphenyl glycidyl ether in the form of a low viscous oil; epoxide content 8.1 equivalents/kg (95.13% of theory).
Workup
- customequipped with thermometer, stirrer, cooler and drip funnel
- temperaturethe batch is heated to 35°-40° C
- washthe resultant solution is washed with 3% NaOH until neutral,
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationThe filtrate is concentrated by rotary evaporation
Sources & evidence
- ORD record
- ord-d41592ac9b864e5fa8d5045e4e4bc7fb
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04724031
Reaction notes
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