dimethyl bicyclo[2.2.2]octane-1,4-dicarboxylate → 4-(Methoxycarbonyl)bicyclo[2.2.2]octane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of Bicyclo[2.2.2]octane-1,4-dicarboxylic acid dimethyl ester (III Example 80, 20.4 g, 89.5 mmol), barium hydroxide octahydrate (14 g, 44.7 mmol) in methanol (160 ml) and water (40 ml) is stirred at 20-25° C. for 18 hour. The mixture is diluted with water (600 ml) and extracted with hexane (150 ml×2). The aqueous mixture is acidified (6 N hydrochloric acid) to pH=1-2 and extracted with chloroform (150 ml 2). The combined chloroform extracts are concentrated. The residue is dissolved in toluene, filtered and concentrated to give the title compound, mp 169-173° C.

Provenance & Evidence