Hydrogen Peroxide → alpha-Pinene oxide

Participants

Reaction Steps

To a mechanically stirred solution of α-pinene (0.01 mol), dodecane (0.001 mol), urea (0.208 mol), sodium bicarbonate (0.003 mol) and manganese sulphate (0.1 mmol) in 10.0 ml of water and 30 ml acetonitrile at 25° C. is added 30% aqueous hydrogen peroxide (0.4 mol) in three equal portions over a period of 3 hours. After 6 hours the reaction mixture was extracted with 4×5 ml diethyl ether. The combined organic layer was dried over anhydrous sodium sulphate. Removal of solvent yielded α-pinene oxide in 85% yield with selectivity 93%.

Provenance & Evidence