- Synthesis of 2,3-Diphenylvinylene sulfone
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2,3-Diphenylvinylene sulfone could be produced through the following synthetic routes.
To a magnetically stirred solution of 6.36 g. (0.0157 mole) of crude α,α'-dibromodibenzyl sulfone (m.p. 135–150°) in 40 ml. of dichloromethane contained in a 100-ml., round-bottomed flask fitted with a reflux condenser there is added in one portion 5.05 g. (0.0500 mole) of triethylamine. The solution is heated at reflux with stirring for 3 hours, filtered, and the precipitate washed with 5 ml. of cold (0°) dichloromethane. The combined dichloromethane solution is washed with two 20-ml. portions of 3 N hydrochloric acid followed by one 10-ml. portion of water. Removal of the solvent by distillation from a water bath at 30° with the aid of a water aspirator gives 3.0 g. (80%) of the vinylene sulfone as a tan solid, m.p. 116–126° (dec.). The crude solid is washed with 5 ml. of cold (0°) ethanol and recrystallized from about 10 ml. of , yielding 2.4–2.5 g. (63–67%) of the pure sulfone as tiny, snow-white needles, m.p. 123–126° (dec.).
Benzene has been identified as a carcinogen; OSHA has issued emergency standards on its use. All procedures involving benzene should be carried out in a well-ventilated hood, and glove protection is required.
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