Toluene → 3-(2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid

Participants

Reaction Steps

In a reaction vessel equipped with a Dean-Stark trap was placed 13.7 grams (0.10 mole) of 3-aminobenzoic acid, 11.4 grams (0.10 mole) of acetonylacetone, 0.10 gram of p-toluenesulfonic acid and 150 ml of toluene. The stirred reaction mixture was heated under reflux for 15.5 hours during which time the theoretical amount of by-product water was collected in the Dean-Stark trap. The reaction mixture was cooled and placed in a separatory funnel where it was washed with two portions of 50 ml each of aqueous 2N sodium hydroxide. The combined base washes were backwashed with 50 ml of toluene then acidified with aqueous 2 N hydrochloric acid. A solid precipitate was collected by filtration and recrystallized from heptane to give 19.3 grams of 3-(2,5-dimethylpyrrol-1-yl)benzoic acid; mp 148°-150° C.

Provenance & Evidence