Hydrochloric Acid → 2,2-Dimethoxycarbonyl-5-chloroindane

Participants

Reaction Steps

To a methanol solution of sodium methylate prepared from 16.04 g of sodium metal and 250 ml of methanol, with ice-cooling, was added a solution of 110.6 g of α,α'-dibromo-4-chloro-o-xylene in 100 ml of anhydrous ether. To the mixture, was added slowly a solution of 46.02 g of dimethyl malonate in 50 ml of anhydrous ether. The mixture was stirred for 48 hours at room temperature to complete the reaction. The reaction mixture was poured into a mixture of 100 ml of 1% aqueous hydrochloric acid solution and ice, and extracted with ether. The aqueous layer was extracted twice with ether. The ether layers were combined, washed with saturated aqueous sodium hydrogencarbonate solution, then with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain 89.4 g of the intended product.

Provenance & Evidence