Acetic Acid → 1,3-Di(4-carboxyphenyl)-5,7-dimethyl adamantane

Participants

Reaction Steps

In the method of Example III, 2.0 grams of 1,3-di(4-methylphenyl)-5,7-dimethyl adamantane were allowed to reflux with 300 ml of acetic acid containing 5.26 grams (0.022 moles) cobalt acetate tetrahydrate and, 2.39 grams cobalt bromide hexahydrate. An oxygen gas flow of 1 cubic foot per hour was bubbled through the refluxing mixture. Over a period of 6 hours, 5.39 grams of 1,3-di(4-methylphenyl)-5,7-dimethyl adamantane were added for a total of 7.39 grams. The reaction mixture was allowed to reflux an additional 28 hours. The reaction mixture was then mixed with water and the mixture was filtered. The resulting filter cake was dissolved in dilute sodium hydroxide. The filtrate was extracted with ether. The ether extracts was evaporated, but gave no residue. The basic solution was acidified with hydrochloric acid followed by an ethyl acetate extraction. Drying and concentration of the ethyl acetate gave 7.12 grams of 1,3-di(4-carboxyphenyl)-5,7-dimethyl adamantane (82% yield), M.P. 252°-255° C.

Provenance & Evidence