Methyl iodide → 4-(Methylthio)phenol

Participants

Reaction Steps

Methyl iodide (18.5 ml) and potassium carbonate (28.7 g) were added to an acetone (250 ml) solution of 4-hydroxythiophenol (25 g) in a water bath, and stirred at room temperature for 5 hours. The salt was removed through filtration, the solvent was evaporated away under reduced pressure, diethyl ether was added to it, and extracted with aqueous 2 N sodium hydroxide solution. The resulting aqueous layer was made acidic with aqueous 6 N hydrochloric acid solution, extracted with diethyl ether, and the organic layer was washed with aqueous saturated sodium chloride solution. After this was dried, the solvent was evaporated away under reduced pressure to obtain 4-(methylsulfanyl)phenol as a pale yellow solid.

Provenance & Evidence