- Preparation of 2,6-Di-tert-butyl-p-benzoquinone
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(CAS NO.: ), with other names as 2,5-Cyclohexadiene-1,4-dione, 2,6-bis(1,1-dimethylethyl)-, could be produced through the following synthetic routes.
A 200-ml., three-necked flask equipped with a mechanical stirrer, a thermometer, and a gas-inlet tube is charged with 41.2 g. (0.200 mole) of 2,6-di-tert-butylphenol in 75 ml. of N,N-dimethylformamide and 2.5 g. (0.0075 mole) of salcomine. With stirring, oxygen is introduced at such a rate that the temperature does not exceed 50°. This is continued for 4 hours, and at the end of the reaction the temperature drops to about 25°. The reaction mixture is then poured onto 500 g. of crushed ice and 15 ml. of 4 N hydrochloric acid. A yellow-brown precipitate is formed, collected by suction filtration, and washed on the filter with three 50-ml. portions of 1 N hydrochloric acid, with three 100-ml. portions of water, and twice with 25-ml. portions of cold ethanol. Drying under reduced pressure at 50° for 3 hours gives 43 g. of crude 2,6-di-tert-butyl as a dark-yellow crystalline solid. Recrystallization from ethanol gives 36.5 g. (83%) of pure 2,6-di-tert-butyl-p-benzoquinone, m.p. 65–66°.
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