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

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Reaction Steps

At room temperature, 8.0 g of anhydrous aluminum chloride and 3.59 g of itaconic acid anhydride were dissolved in distilled tetrachloroethane, 20 ml, with vigorous agitation. Then the solution was cooled on an ice-water bath and to this, 2-ethybenzofuran, 4.39 g, dissolved in 10 ml of tetrachloroethane were added dropwise. After three hours stirring in an ice-water bath followed by 12 hrs. stirring at room temperature, the reaction mixture was poured into ice-water, 80 g, containing 20 ml of HCl and extracted with ethyl acetate. The ethyl acetate layer was extracted with 50 ml of a 10% NaCO3 solution and then the aqueous layer was acidified with 10% HCl again and extracted with ethyl acetate. After washing with water, drying and removal of the solvent, the resulting viscous oily substance was extracted with ligroin (20 ml×3). Needle-like crystals were obtained after overnight standing at room temperature.

Provenance & Evidence