2,3-Dicyanohydroquinone (10 g) and glacial acetic acid (100 ml) were heated to gentle reflux in a three-necked flask fitted with a stirrer, condenser, and gas inlet tube. Dry chlorine was then passed into the clear solution at a rate of about 0.2 g per minute and after 1 hour a crystalline solid began to separate from the refluxing solution. After a further 30 minutes, chlorination was stopped, the contents of the flask cooled to room temperature, and the solid separated by filtration. It was washed with chloroform (50 ml) and dried. The yield of chunky white crystals was 6.4 g (44%). The product was practically insoluble in hot water and could be crystallized from aqueous ethanol as needles, unchanged on heating to 300° (according to Thiele, it blackens at 265°).
© Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru