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ChemicalBook CAS DataBase List Isophorone oxide
10276-21-8

Isophorone oxide synthesis

9synthesis methods
In a three-necked flask equipped with a dropping funnel, a mechanical stirrer, and a thermometer, a solution of 55.2 g (0.4 mol) of isophorone and 115 ml (1.2 mol) of 30% aqueous hydrogen peroxide in 400 ml of methanol. After the contents of the flask have been cooled to 15 ℃ using an ice bath, 33 ml (0.2 mol) of 6N aqueous sodium hydroxide is added, dropwise and with stirring, over 1 hour. During the addition, the temperature of the reaction mixture is maintained at 15–20℃ with a bath of cold water. After the addition is complete, the resulting mixture is stirred for 3 hours as the reaction mixture temperature is maintained at 20–25℃. The reaction mixture is then poured into 500 ml. of water, and the resulting mixture is extracted with two 400-ml portions of ether. The combined extracts are washed with water and dried over anhydrous magnesium sulfate. After the bulk of the ether has been removed by distillation (or flash distillation) through a 30-cm. Vigreux column at atmospheric pressure, the residual liquid is distilled through the Vigreux column under reduced pressure. The yield of isophorone oxide is 43–44.5 g. (70–72%).
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Yield:-

Reaction Conditions:

with tert.-butylhydroperoxide;N-hydroxyphthalimide;Cu3Al(OH)2(7+)*3.5CO3(2-) in acetonitrile at 90; for 24 h;Catalytic behavior;Reagent/catalyst;Temperature;

Steps:


Typically, the catalytic reactions were carried out in a 50 mL round flask. Cu-Al HTLcs (150 mg), NHPI (0.75 mmol), and acetonitrile (10 mL) were placed in a flask equipped with a magnetic stirrer, then the mixture was stirred vigorously for 10 min to create a finely dispersed heterogeneous system. Sequentially, isophorone (10 mmol) and 70 mass % TBHP (40 mmol) were added and the reaction mixture was refluxed. After the required time, the reaction mixture was cooled and filtered. Next, saturated NaHSO3 solution was added to the solution to remove any extra TBHP and the solution was extracted with ethyl acetate (3 × 10 mL). The organic phase was washed successively with saturated EDTA solution and saturated NaCl solution and dried overanhydrous Na2SO4. The solvent was removed by rotary evaporation and the resulting residue was analysed by GC.

References:

Zhou, Yin;Tang, Rui-Ren;Song, Dan [Chemical Papers,2016,vol. 70,# 7,p. 888 - 897]

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