Methanesulfonic Acid → HCID 13637980, compound

Participants

Reaction Conditions

Reaction Steps

5-Phenyl-3-(2-thienylmethylene)-2-furanone (34.9 g), methanesulfonic acid (170 cc) and glacial acetic acid (170 cc) are heated for one hour at 120° C. The mixture is cooled to 40° C., poured onto crushed ice and extracted with methylene chloride. The organic phase is washed with water and extracted with a normal sodium hydroxide solution. The basic aqueous phase is washed with methylene chloride, acidified to pH 1 by adding an aqueous hydrochloric acid solution and extracted with methylene chloride. The precipitate formed is filtered, the organic phase is dried over magnesium sulfate and evaporated under reduced pressure. The evaporation residue and the precipitate are combined and chromatographed on silica gel using ethyl acetate as the eluent. 4-Phenylbenzo[b]thiophene-6-carboxylic acid (17.4 g), m.p. 222° C., is thereby isolated.

Provenance & Evidence