Methyl iodide → 3-(Methylsulfanyl)phenol

HRID 1862142Notes

Reaction equation

HRID 1862142 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O.O>[CH3:9][S:8][C:4]1[CH:3]=[C:2]([OH:1])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27366133-Hydroxybenzenethiol

Product 1

HCID 99204073-(Methylsulfanyl)phenol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

3-Hydroxythiophenol (5.0 g, 39.7 mmol) and potassium carbonate (6.03 g, 43.6 mmol) were stirred in acetone (80 mL) at 0° C. Iodomethane (2.5 mL, 40 mmol) was added dropwise, and the reaction stirred for 45 min. The solution was diluted with H2O (150 mL) and extracted with EtOAc (2×100 mL). Organics were washed with brine (100 mL), dried (Na2SO4) and concentrated in vacuo. Purification by silica gel chromatography (25% EtOAc/hexanes) 5.08 g (91%) of 3-methylsulfanyl-phenol as a clear oil. 1H NMR (300 MHz, CDCl3) δ 7.15 (t, 1H, J=8.1 Hz), 6.82 (d, 1H, J=8.1 Hz), 6.74 (t, 1H, J=1.8 Hz), 6.60 (dd, 1H, J=8.1, 1.8 Hz), 4.86 (s, 1H), 2.47 (s, 3H).

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. washOrganics were washed with brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (25% EtOAc/hexanes) 5.08 g (91%) of 3-methylsulfanyl-phenol as a clear oil

Sources & evidence

ORD record
ord-63a41667c4e241d68cf49168b446b670
Source dataset
uspto-grants-2003_03
Patent number
US06534524B1

Reaction notes

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