Sulfuric Acid → 1-Hydroxyadamantan-2-one

Participants

Reaction Steps

To 25 ml of acetic acid were added 10 mmol of adamantane, 1 mmol of N-hydroxyphthalimide, 0.05 mmol of 98% by weight sulfuric acid and 0.05 mmol of acetylacetonatovanadium V(AA)3, and the resultant mixture (pH 1.7) was stirred under an oxygen atmosphere at a temperature of 75° C. for 6 hours. The products in the reaction mixture were analyzed by gas chromatography, and, as a result, adamantane was converted into adamantanone (yield 25%) and 1-hydroxyadamantanone (yield 29%) with a conversion of 96%. Incidentally, excepting the above, 1-adamantanol (yield 10%), 1,3-adamantanediol (yield 12%) and other products (polyketone such as adamantanedione) (yield 20%) were formed.

Provenance & Evidence