Synthesis of Para-Benzoquinone

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From hydroquinone Using CrO3 [1] Cool a solution of 33 g (0.

33 mol) of hydroquinone in 150 ml of 60% acetic acid contained in a 600 ml beaker to below 5 C in an ice bath. Dissolve 42 g (0.42 mol) of chromium trioxide (CAUTION !!!) in 70 ml of water, and add 30 ml of glacial acetic acid. By means of a separatory funnel with bent stem and supported over the beaker, add the chromium trioxide solution to the mechanically stirred hydroquinone solution at such a rate that the temperature does noot rise above 10 C; the addition takes 2 hours. Filter the mixture at once and wash the quinone several times with 10 ml portions of ice cold water. Spread the material upon filter paper until dry but no longer or the quinone will be lost through sublimation. The yield of quinone (a bright yellow crystalline solid) is 21 g (66 %), M.P.: 115 C. It darkens when exposed to light. Impure quinone may be purified by placing it in a distilling flask attached to a condenser and passing a rapid steam into the flask: the quinone sublimes and collects in the receiver. It is separated from the water by filtration and dried; the M.P. is 116 C. The vapour has a penetrating odour and attacks the eyes.

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