Water → 2,5-Diphenylbenzene-1,4-dicarboxylic acid

Participants

Reaction Conditions

Reaction Steps

2′,5′-Dimethyl-1,1′:4′,1″-terphenyl (180.9 g) was dissolved in pyridine (4296 mL), water (405 mL) was added and the reaction mixture heated to 90° C. Potassium permanganate (KMnO4) (516 g, Sigma-Aldrich) was carefully added and refluxing continued. Additional KMnO4 (235 g) and water (677 mL) were added every 30 minutes for 2 hours. Once addition was complete, refluxing was continued for 18 hours. The reaction mixture was filtered hot through a celite pad, washing the filter cake with boiling water (3×2000 mL). The filtrates were concentrated to remove most of the pyridine before adjusting to pH-1 with concentrated hydrochloric acid. The solids were collected by vacuum filtration, washed with water (2×1400 mL) and dried to give a cream solid. The solid was then refluxed in ethyl acetate (840 mL), cooled, collected by vacuum filtration and washed with ethyl acetate (2×233 mL) to give the product as a cream solid. Yield; 183.8 g.

Provenance & Evidence