Methyl iodide → 4-(Methylthio)phenol

Participants

Reaction Steps

In a water bath, 18.5 ml of methyl iodide and 28.7 g of potassium carbonate were added to an acetone (250 ml) solution of 25 g of 4-hydroxythiophenol, 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 the residue, and extracted with aqueous 2 N sodium hydroxide solution. The obtained aqueous layer was acidified with aqueous 6 N hydrochloric acid solution, extracted with diethyl ether, and the organic layer was washed with aqueous saturated sodium chloride solution. After dried, the solvent was evaporated away under reduced pressure to obtain 27.3 g of 4-(methylsulfanyl)phenol as a pale yellow solid. In a water bath, 67 ml of aqueous 30% hydrogen peroxide solution was gradually and dropwise added to an acetic acid (130 ml) solution of 27.3 g of 4-(methylsulfanyl)phenol. After the addition, this was gradually heated up to 100° C., and stirred for 1 hour. The reaction liquid was restored to room temperature, and neutralized with aqueous saturated sodium bicarbonate. This was extracted with ethyl acetate, washed with aqueous saturated sodium bicarbonate and saturated saline water. After dried, the solvent was evaporated away to obtain 31.6 g of the entitled compound as a pale yellow solid.

Provenance & Evidence