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 Synthesis of Methyl phenyl sulfoxide
  • Synthesis of Methyl phenyl sulfoxide
  • Methyl phenyl sulfoxide (CAS NO.: ), which is also known as , (methylsulfinyl)-, could be produced through the following synthetic routes.

    Synthesis of Methyl phenyl sulfoxide

    In a 500-ml. round-bottomed flask equipped with a magnetic stirrer are placed 22.5 g. (0.105 mole) of powdered sodium metaperiodate and 210 ml. of water. The mixture is stirred and cooled in an ice bath, and 12.4 g. (0.100 mole) of thioanisole is added. The reaction mixture is stirred for 15 hours at ice-bath temperature and is then filtered through a Büchner funnel. The filter cake of sodium iodate is washed with three 30-ml. portions of methylene chloride. The water-methylene chloride filtrate is transferred to a separatory funnel, the lower methylene chloride layer is removed, and the water layer is extracted with three 100-ml. portions of methylene chloride. The combined methylene chloride extracts are treated with activated carbon and dried over anhydrous sodium sulfate. The solvent is removed at reduced pressure to yield 13.6–13.9 g. of a slightly yellow oil which crystallizes on cooling. The crude sulfoxide is transferred to a 25-ml. distillation flask with the aid of a small amount of methylene chloride. After removal of the solvent, a pinch of activated carbon is added to the distillation flask. Simple vacuum distillation of the crude product through a short path still affords 12.7–12.8 g. (91%) of pure methyl phenyl sulfoxide, b.p. 78–79° (0.1 mm.), m.p. 33–34°.


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