Methyl iodide → 4-(Methylthio)phenol

HRID 1671657Notes

Reaction equation

HRID 1671657 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)phenol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  1. customThe salt was removed through filtration
  2. customthe solvent was evaporated away under reduced pressure, diethyl ether
  3. additionwas added to it
  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 this was dried
  8. customthe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-2ac6b3d353d64f65950f809ed595f78b
Source dataset
uspto-grants-2011_08
Patent number
US07994331B2

Reaction notes

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