Acetic Acid → 5-(Phenylethynyl)adamantane-1,3-dicarboxylic acid

Participants

Reaction Conditions

Reaction Steps

Under the atmosphere of nitrogen gas, 10 g (73 mmole) of adamantane, 1.2 g (7.4 mmole) of N-hydroxyphthalimide, 80 mg (0.31 mmole) of cobalt(II) acetylacetonate, 9.2 g (90 mmole) of ethynylbenzene and 150 ml of acetic acid were stirred. To the resultant mixture, a mixed gas containing 2.0 liters of carbon monoxide and 0.50 liters of oxygen was introduced under a pressure of 7.5 kg/cm2, and the mixture was stirred at 60° C. for 12 hours. The reaction fluid was added into a 5 mole/liter aqueous solution of hydrochloric acid cooled at 0° C., and the solid substance was recovered by filtration. The obtained solid substance was purified in accordance with the liquid chromatography and recrystallization, and 5-(phenylethynyl)adamantane-1,3-dicarboxylic acid was obtained.

Provenance & Evidence