Sulfuric Acid → 3-Chloro-4-methylphenol

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Reaction Steps

283 g of 3-chloro-4-methylaniline was added to a solution of 1000 ml of water and 500 ml of concentrated sulfuric acid, causing the temperature of the mixture to rise from ambient to 95° C. The mixture was cooled and stirred at room temperature for 30 minutes, then cooled to 5° C. and a solution of 145 g of sodium nitrite in 500 ml of water was slowly added (1.5 hours) to the stirred mixture at 5°-10° C. The mixture was stirred at about 5° C. for one hour, then added over two hours to a stirred solution of 1.2 liters of concentrated sulfuric acid in 2 liters of water, at 105°-110° C. The resulting mixture was stirred at 110° C. for one hour, then held at room temperature for 18 hours. Then 3.5 liters of hexane was added, the mixture was stirred for 30 minutes, allowed to stand, and the two liquid phases were separated. The hexane phase was filtered, washed with water, dried (MgSO4) and concentrated to dryness to give crude 3-chloro-4-methylphenol (2A).

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