Methyl iodide → 1-Chloro-4-[(4-methoxybutyl)sulfanyl]benzene

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Reaction Steps

To a mixture of 7.2 g of a 57% oil dispersion of sodium hydride and 125 ml of toluene was added a solution of 36.5 g of 4-(p-chlorophenylthio)butanol in 125 ml of toluene. The mixture was stirred and heated under reflux until the evolution of hydrogen ceased. It was then cooled and 25.6 g of methyl iodide was added with stirring. The resulting mixture was heated under reflux for 2 hours, cooled, washed with three portions of water saturated with sodium chloride, dried over anhydrous sodium sulfate and evaporated to dryness. The residue was distilled at reduced pressure to give 17.1 g of product, b.p. 92°-100° at 0.05 mm, ND25 1.5524.

Provenance & Evidence