N-Hydroxyphthalimide → 5-Hydroxy-1,3-adamantanedicarboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.92 mol of 1,3-adamantanedicarboxylic acid, 192 mmol of N-hydroxyphthalimide, 1.83 mmol of cobalt (II) acetylacetonato and 1290 ml of acetic acid was stirred at 80° C. under an oxygen atmosphere (1 atm) for 24 hours. The reaction mixture was concentrated and then separated by the addition of ethyl acetate and water. Sodium chloride was added to the aqueous layer and the layer was extracted with ethyl acetate; the organic layer was dried on anhydrous magnesium sulfate and was concentrated. The caked crude purified product was washed with ethyl acetate to give 5-hydroxy-1,3-adamantanedicarboxylic acid (yield: 52.5%) at a conversion rate from 1,3-adamantanedicarboxylic acid of 75%.

Provenance & Evidence