Methyl iodide → 4-(Methylthio)phenol

HRID 2080689Notes

Reaction equation

HRID 2080689 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, 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.

Workup

  1. customThe salt was removed through filtration
  2. customthe solvent was evaporated away under reduced pressure, diethyl ether
  3. additionwas added to the residue
  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-a0845604c33c47d7a2cb0d468b576606
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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