Isopropanol → Tertiary-butylperoxy octadecyl carbonate

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Reaction Steps

Tertiary-butylperoxy octadecyl carbonate was prepared by reaction of tertiary-butyl hydroperoxide with octadecyl chloroformate. Tertiary-butyl hydroperoxide, 70 percent (27.0 grams, 0.21 mole) was placed in a flask, and sodium hydroxide, 20 percent (43.3 grams, 0.22 mole) was added slowly at lower than 20° C., followed by the addition of 10.0 grams of isopropanol all at once. Octadecyl chloroformate (66.5 grams, 0.20 mole) and hexane (115.8 grams) were combined in an addition funnel and added over a period of 90 minutes at about 35° C. The resulting mixture wa phase-separated and the organic layer was washed with three 100 milliliter portions of water. Yield was 179.9 grams, 93.2 percent by weight of theoretical.

Provenance & Evidence