4-(Methylthio)phenol → 4-(Methylsulfonyl)phenol

Temperature

100 °C

In a water bath, methyl iodide (18.5 ml) and potassium carbonate (28.7 g) were added to an acetone (250 ml) solution of 4-hydroxythiophenol (25 g), and stirred at room temperature for 5 hours. The salt was removed by filtration, the solvent was evaporated away under reduced pressure, diethyl ether was added, and extracted with aqueous 2 N sodium hydroxide solution. The obtained 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 dried, the solvent was evaporated away under reduced pressure to obtain 4-(methylsulfanyl)phenol (27.3 g) as a pale yellow solid. In a water bath, 30% hydrogen peroxide water (67 ml) was gradually and added dropwise to an acetic acid (130 ml) solution of 4-(methylsulfanyl)phenol (27.3 g). After the addition, this was gradually heated up to 100° C., and stirred for 1 hour. The reaction solution was restored to room temperature, and neutralized with saturated sodium bicarbonate water. This was extracted with ethyl acetate, and washed with saturated sodium bicarbonate water and saturated saline water. After dried, the solvent was evaporated away to obtain the entitled compound as a pale yellow solid.

1. additionAfter the addition
2. customwas restored to room temperature
3. extractionThis was extracted with ethyl acetate
4. washwashed with saturated sodium bicarbonate water and saturated saline water
5. customAfter dried
6. customthe solvent was evaporated away

ORD record

ord-56491c50bbb74d8d9412eb6d0aca95f5

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07799820B2