Formic Acid → 4-(2,3-Epoxypropyl)-2,6-dimethylphenyl glycidyl ether

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Reaction Steps

A 350 ml sulfurating flask equipped with thermometer, stirrer, cooler and drip funnel is charged with 21.8 g (0.10 mole) of 4-allyl-2,6-dimethylphenyl glycidyl ether, 10.9 g (0.24 mole) of formic acid and 135 ml of chloroform. At room temperature, 23.2 g (0.47 mole) of hydrogen peroxide are then added dropise over 4 hours. The reaction miture is held at this temperature overnight. It is subsequently taken up in chloroform and the resultant solution is washed twice with 3% NaOH solution until neutral, made peroxide-free with sodium sulfite, dried over sodium sulfate and filtered. The filtrate is concentrated, affording 20.03 g (80.50% of theory) of 4-(2,3-epoxypropyl)-2,6-dimethylphenyl glycidyl ether in the form of a low viscous resin; epoxide content 7.7 equivalents/kg (90.11% of theory).

Provenance & Evidence