Methyl iodide → 4-(Methylthio)phenol

HRID 1715314Notes

Reaction equation

HRID 1715314 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1>CC(C)=O>[CH3:3][S:16][C:13]1[CH:14]=[CH:15][C:10]([OH:9])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

Product 1

HCID 140864-(Methylthio)phenolYield 98.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  1. customThe salt was removed by filtration
  2. customthe solvent was evaporated away under reduced pressure, diethyl ether
  3. additionwas added
  4. extractionextracted with aqueous 2 N sodium hydroxide solution
  5. extractionextracted with diethyl ether
  6. washthe organic layer was washed with aqueous saturated sodium chloride solution
  7. customAfter dried
  8. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-4e374ea3b1984c32925717f89ca09fcb
Source dataset
uspto-grants-2010_09
Patent number
US07799820B2

Reaction notes

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