Aluminum(III) Chloride → HCID 13588806, compound

Participants

Reaction Steps

21.1 g (0.16 mole) of aluminum chloride was quickly added to 50 cc of nitrobenzene at ambient temperature. Then a solution of 11.3 g (0.058 mole) of (5-methyl-2-thienyl) succinic anhydride in 30 cc of nitrobenzene was added drop by drop in 1 hour 30 minutes. The mixture was stirred for 5 hours at ambient temperature then poured into an ice-hydrochloric acid mixture and extracted with methylene chloride. The organic phase was separated and extracted with an aqueous solution of sodium carbonate. The aqueous phase was acidified with dilute hydrochloric acid then extracted with ethyl acetate. The organic solution was washed with water, dried on sodium sulfate and concentrated under reduced pressure. 7.7 g (yield=68%) of 2-methyl-4-oxo-5,6-dihydro-4H-cyclo-penta[b]thiophene-6-carboxylic acid melting at 137°-139° C. was obtained. By recrystallization in a hexane-ethyl acetate mixture, a product was obtained with a melting point of 140°-143° C. identical in all respects with that obtained in example 2.

Provenance & Evidence