Hydrochloric Acid → HCID 20329637, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6.9 g of sodium nitrite in 40 ml of water was added drop-by-drop to a stirred mixture of 30 g of 12C and 160 ml of 6 N hydrochloric acid, the rate of addition being adjusted to maintain the temperature of the reaction mixture at 0°-5° C. The mixture was stirred for 1 hour at 0°-5° C., then added with vigorous stirring, to 50 ml of 20% aqueous cuprous chloride heated to 70° C. The resulting mixture was heated to 70° C., then allowed to cool. The solid was collected, washed with water, dried (P2O5, reduced pressure) and dissolved in tetrahydrofuran. The solution was suspended on 75 g of silica gel and dry column chromatographed, using chloroform as eluent. The product was removed from the combined appropriate fractions with tetrahydrofuran. The solvent was evaporated ad the residue was dried (drying pistol, P2O5, refluxing acetone) to give ethyl 5-(4-chlorophenyl)benzofuran-2-carboxylate (12 D), mp 108°-110° C.

Provenance & Evidence