Hydrochloric Acid → 2-Methylene-4-oxo-4-(2-ethyl-3-benzofuranyl)butyric acid

Participants

Reaction Steps

A suspension of 8.0 g of anhydrous aluminum chloride and 3.59 g of itaconic acid anhydride in dried tetrachloroethane was stirred for one hour at room temperature. To this solution, 4.39 g of 2-ethylbenzofuran dissolved in 10 ml of tetrachloroethane was added dropwise under cooling by ice-water. And then stirring was continued for 3 hrs. in ice-water and for 12 hrs. at room temperature. The reaction mixture was poured into the mixture of 80 g of ice and 20 ml of conc. HCl, then extracted with ethylacetate (50 ml). After washed with water, the solvent layer was made alkaline with 10% NaCO3 solution. The water layer was acidified with 10% HCl again and then was extracted with ethylacetate. The brown viscous residue obtained after washing, drying and removal of ethyl acetate layer, was extracted with ligroin. After standing overnight, the needle-like crystals were obtained.

Provenance & Evidence