Sulfuric Acid → 3,5,5-TRIMETHYL-3-(t-BUTYLPEROXY)CYCLOHEXANONE

Participants

Reaction Conditions

Reaction Steps

A reaction mixture of 6.9 g. (0.05 mole) of isophorone, 23.20 g. (0.2 mole) of dry 81% t-butyl hydroperoxide and 25 ml. of pentane was cooled to 10° C. and 5.70 g. of 77% sulfuric acid added slowly over 45 minutes. The reaction mixture was allowed to warm to 25° C. and stirred at 25° C. for five hours. The pentane solution of the product was washed with water, and sodium bisulfite solution and then dried over anhydrous magnesium sulfate. The product weighing 9.35 g., was obtained by stripping under reduced pressure (60.4% recovery). The infrared spectrum had a strong absorption in the 880 cm-1 region usually associated with t-butylperoxy groups. Iodometric assay showed the presence of active oxygen and the GLC scan of the product showed a large peak for the expected product.

Provenance & Evidence