N-Hydroxyphthalimide → 3-Hydroxyadamantane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 5.07 mol of 1-adamantanecarboxylic acid, 507 mmol of N-hydroxyphthalimide, 5.07 mmol of cobalt (II) acetylacetonato and 12500 ml of acetic acid was stirred at 75° C. under an oxygen atmosphere (1 atm) for 8 hours. The reaction mixture was concentrated, and was subjected to column chromatography on a silica gel (eluent: chloroform/methanol (8/1)), and the obtained purified product was further recrystallized with ethanol/n-hexane to give 3-hydroxy-1-adamantanecarboxylic acid (yield: 38%) at a conversion rate from 1-adamantanecarboxylic acid of 99%.

Provenance & Evidence