Carbon Dioxide → 3-(1-Adamantyl)-4-methoxyethoxymethoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

The above compound (a) (28.5 g, 72 mmol) was dissolved in 200 ml of THF. The solution obtained was added dropwise to magnesium (2.4 g, 100 mmol) and a crystal of iodine. After introduction, the mixture was heated at reflux for two hours, cooled to -78° C. and a stream of CO2 was passed therethrough for one hour. The reaction medium was permitted to warm to room temperature and was then poured into saturated aqueous ammonium chloride solution and extracted with ethyl ether. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was triturated from hexane, filtered and dried. 15.5 g (60%) of the expected acid, having a melting point of 115°-6° C., were recovered.

Provenance & Evidence