Sulfuric Acid → 2-(3,5-Dimethyladamantan-1-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

Concentrated sulfuric acid (44 mL) and boron trifluoride etherate (3.53 mL) were added to a flask and cooled to 8° C. A solution of 1-bromo-3,5-dimethyladamantane (11.02 g) in 1,1-dichloroethylene (35.3 mL) was added dropwise over a 2 hour period. The temperature was kept between 14 and 18° C. and gas evolution was observed. After stirring 1 hour at 10° C., the reaction was worked up by adding to ice and extracting with diethyl ether. The organic layer was extracted with 1N NaOH (3×), and the combined aqueous solution was acidified with sulfuric acid and re-extracted with ether (3×). The organic layers were combined, dried over magnesium sulfate, filtered and evaporated to dryness to give crude 3,5-dimethyladamantaneacetic acid (6.23 g).

Provenance & Evidence