Methyl Acrylate → Tetracyclo(6.6.2.0^(2,7).0^(9,14))hexadeca-2,4,6,9,11,13-hexaene-15-carboxylic acid

Participants

Reaction Steps

Anthracene (40 gm) was combined with methyl acrylate (30 gm) in a Parr bomb and heated to 150°-175° C. for 6 hours. The mixture was allowed to remain in the bomb at room temperature for 72 hours. The mixture was dissolved in methanol (225 ml), treated with a solution of potassium hydroxide (40 gm) in water (40 ml) and heated to reflux for 4 hours. The solution was cooled to room temperature and most of the solvent was removed on a rotary evaporator. The residue was dissolved in water (200 ml), filtered through charcoal and acidified with concentrated hydrochloric acid. The resulting mixture was allowed to stand overnight and the precipitate was filtered. The white solid was dried at 80° and recrystallized from benzene to provide the product (mp=188°-189° C.).

Provenance & Evidence