Hydrochloric Acid → HCID 54347228, compound

Participants

Reaction Steps

9.0 g. 4-Carboxymethoxy-benzaldehyde (see Example 5) and 8.2 g. 4-acetylbenzoic acid were dissolved in 50 ml. 10% aqueous sodium hydroxide solution and the solution stirred at ambient temperature for 2.25 hours. 150 ml. Ethanol were added and the solid precipitate obtained was filtered off, washed with ethanol and dried to give 16.9 g. disodium 4'-carboxy-4'-carboxymethoxy chalcone. This disodium salt was converted into the acid by dissolving in water, acidifying the solution with concentrated hydrochloric acid, filtering off the solid obtained, washing with water and drying, the yield being 15.1 g. Thin layer chromatography showed the presence of about 7% of polar impurities, most of which were removed by refluxing the solid with methanol, filtering and drying the undissolved solid, the yield being 11.9 g. Thin layer chromatography then showed the product to be about 98% pure. The solid was dissolved in dimethyl formamide and the solution was filtered and evaporated to a small volume. 200 ml. Methanol was added and the solid precipitate obtained was filtered off, washed with methanol and dried to give 8.0 g. of product, thin layer chromatography of which showed it to be more than 99% pure. The 4'-carboxy-4-carboxymethoxy-chalcone thus obtained had a melting point of 312°-314° C.

Provenance & Evidence