Oxygen → Adamantanone

Participants

Reaction Steps

A mixture of 0.1 mol of 2-adamantanone, 10 mmol of N-hydroxyphthalimide, 0.33 mmol of acetylacetonatovanadium V (AA)3, 0.17 mmol of acetylacetonatomanganese Mn(AA)3, and 250 ml of acetic acid was stirred at 85° C. in an oxygen atmosphere (1 atm) for 10 hours. The resulting reaction mixture was concentrated and was then extracted with ethyl acetate. A portion of an organic layer was concentrated and was then cooled for crystallization to yield 5-hydroxy-2-adamantanone of the following formula in a yield of 48% with a conversion rate from 2-adamantanone of 74%.

Provenance & Evidence