3,3-bis(4-fluorophenyl)propanoic Acid → 3-(4'-Fluorophenyl)-6-fluoro-1-indanone

Participants

Reaction Steps

A solution of 850 grams of 3,3-bis(4-fluorophenyl)-propanoic acid in 600 milliliters of thionylchloride was refluxed for two hours and then concentrated in vacuo. The crude acid chloride was taken up in 2 liters of carbondisulfide. 850 grams of aluminiumchloride were added while stirring and cooling at a temperature of 10-15 degrees Centigrade. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then poured unto crushed ice, and one liter of concentrated hydrochloric acid was added. The mixture was extracted with methylene chloride, and the organic phase was extracted with water and 1 N sodium hydroxide solution. The organic phase was then dried over anhydrous magnesium sulfate, treated with active carbon and concentrated in vacuo. The residue was taken up in hot diisopropylether, an insoluble oil was separated by decanting, and the isopropylether extract was cooled. The crystals which separated out were sucked off and dried to give 670 grams of 3-(4'-fluorophenyl)-6-fluoro-1-indanone melting at 70-73 degrees Centigrade.

Provenance & Evidence