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Synthesis of allyl hydroperoxide

Allyl hydroperoxide is an extremely unstable compound that must be kept away from all forms of heat and friction. A small amount of rather excessive precautions, namely the use of a red light when preparing or handling the compound, are quite necessary. This compound is stable under UV light but normal light can be hazardous. Like all explosive peroxides, this one does not want to exist for long. I would suggest keeping it refrigerated and in the dark to avoid an untimely detonation.


C3H6O2
b.p. ? °C mass 74.10 g/mol
m.p. detonates CAS# 6069-42-7
den. ? g/mL v.det. ? m/s

2-propenyl hydroperoxide
hydroperoxide, 2-propenyl (9CI)


allyl hydroperoxide

allyl hydroperoxide

Prepare a solution of 10.8 g of allyl methanesulfonate and 40 mL of 30% hydrogen peroxide dissolved in 30 mL of methyl alcohol in a small beaker. Prepare a second solution of 10.1 g of potassium hydroxide dissolved in 10.1 mL of water, cool this solution to 0 °C and keep it in a salt-ice bath. With extreme caution, add the allyl methanesulfonate solution by dropwise addition to an Erlenmeyer flask containing the potassium hydroxide solution in the salt-ice bath using a dropper pipette or a burette. The addition must be completed in a room illuminated with one of those darkroom red lights as other light will cause the allyl hydroperoxide to explode, a safer bet would be to cover all glassware with aluminum foil to keep out all light. The product is purified by vacuum distillation followed by extraction with ethyl ether. It can be further purified by liquid chromatography. The yield is quite low, 58 mg after chromatographic distillation. You will need a graduated cylinder to measure liquids and a thermometer to check the temperature.

While a good faith effort has been made to ensure the accuracy of all scientific information presented on this page, the possibility exists that some errors have invaded the machine. Furthermore, there may be certain omissions of physical properties, reaction conditions, necessary equipment, storage and handling requirements, and critical safety data. As with any scientific endeavor, especially chemistry, the necessary safety precautions should be observed at all times.

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