p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

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Reaction Steps

p-Nitrobenzyl bromide (21.6 g, 100 mmol) and the salt G (25.5 g, 100 mmol) were dissolved in anhydrous dimethylformamide (100 ml), and the solution was stirred at room temperature for 24 hours. The reaction mixture was then diluted with ethyl acetate (300 ml), washed with saturated NaHCO3, brine, dried (Na2SO4), and concentrated in vacuo to yield ester H as a viscous oil (36.5 g). This material, quite pure as determined by TLC, was then dissolved in 1,4-dioxane (80 ml) to which was added p-toluenesulfonic acid monohydrate (19.02 g, 100 mmol). After stirring at room temperature for 20 hours, the product precipitated from solution, was filtered, washed with ether, and dried to yield the p-toluenesulfonate salt (36.04 g, 84.0% from G) as a white, fluffy, solid, mp 142°-3°.

Provenance & Evidence