Hydrochloric Acid → 3-Methoxybenzenesulfonyl chloride

Participants

Reaction Conditions

Reaction Steps

61.6 gm (0.5 mol) of m-anisidine were dissolved in 50 ml of glacial acetic acid, and the solution was admixed dropwise with 110 ml of concentrated aqueous hydrochloric acid. The mixture was cooled to 0° C. and diazotized with a solution of 38 gm (0.551 mol) of sodium nitrite in 75 ml of water. After stirring for 10-15 minutes, the reaction mixture was poured slowly to a mixture of 24 gm (0.14 mol) of copper (II) chloride, 5 gm of copper(I)chloride, 300 ml of a 30% solution of sulfur dioxide in glacial acetic acid and 450 ml of benzene, whereby a strong evolution of gas and an increase in the temperature up to 40° C. was observed. As soon as the reaction temperature dropped, the mixture was heated for 1 hour at 40° C. After cooling, the reaction mixture was diluted with 2.5 liters of ice water, filtered and the organic phase was separated. The organic phase was washed with water and sodium bicarbonate solution and evaporated.

Provenance & Evidence