Aluminum(III) Chloride → HCID 13588806, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 11.3 g (0.058 mole) of (5-methyl-2-thienyl) succinic anhydride in 30 cc of methylene chloride was added drop by drop to a mixture of 21.1 g (0.16 mole) of aluminum chloride and 50 cc of methylene chloride cooled to 0° C. The reaction mixture was stirred 5 hours at ambient temperature then poured into an ice-hydrochloric acid mixture and extracted with methylene chloride. The organic phase was separated then extracted with an aqueous sodium bicarbonate solution. The aqueous phase was acidified then, after filtration of an insoluble, again extracted with ethyl acetate. The organic extract was washed, dried on sodium sulfate and concentrated dry under reduced pressure. Recrystallization of the residue provided 3.2 g (yield=28%) of 2-methyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophene-6-carboxylic acid (mp=140°-143° C.) identical in all respects to that obtained in example 2.

Provenance & Evidence