3-(3,4-Dichlorophenyl)propionic acid → 5,6-Dichloro-2,3-dihydro-1H-inden-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 20 g of 3-(3,4-dichlorophenyl)-propionic acid [J. Med. Chem., Vol. 16(2) (1973), p. 101-106 ] and 100 ml of thionyl chloride was refluxed for 30 minutes and the thionyl chloride was then evaporated. The residue was taken up in 20 ml of methylene chloride and the solution was poured into a suspension of 20 g of aluminum chloride in 150 ml of methylene chloride. The mixture was stirred for one hour at room temperature and 30 minutes at 50° C. The mixture was poured over ice and was stirred for 30 minutes and then was extracted with methylene chloride. The organic phase was washed with water, dried and evaporated to dryness and the residue was taken up in ether and vacuum filtered. The product was dried to obtain 80 g of the desired product melting at 155° C.

Provenance & Evidence