P-Cresol → 4-Methyl-2-(methylthio)phenol

HRID 1154282Notes

Reaction equation

HRID 1154282 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[CH3:9][S:10]SC>C1(C)C=CC=CC=1>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([OH:7])=[C:1]([S:10][CH3:9])[CH:2]=1

Participants

4

Reactant 2

HCID 2879P-CresolHCID 12232Dimethyl Disulfide

Product 1

HCID 131993354-Methyl-2-(methylthio)phenolYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of para-cresol (65 grams, 0.60 moles) and toluene (20 ml) was distilled until the mixture was free of toluene. Aluminum turnings (1.1 grams, 0.04 gram atoms) were then added to the dried para-cresol and this mixture was heated at 150°-160° C. until cessation of hydrogen evolution. Methyldisulfide (36 ml. 0.4 moles) was added and the mixture heated at reflux (about 160° C.) overnight. The mixture was refluxed for another additional 4 hours and was then flashed under a vacuum. The flashed mixture was then distilled through a 0.7×30 cm packed column to yield 30.3 grams of 4-methyl-2-(methylthio)-phenol, a 55 percent yield. Subsequently, ⟦MMR⟧ NMR analysis verified the identity of the compound.

Workup

  1. distillationwas distilled until the mixture
  2. additionAluminum turnings (1.1 grams, 0.04 gram atoms) were then added to the dried para-cresol
  3. temperaturethis mixture was heated at 150°-160° C. until cessation of hydrogen evolution
  4. temperaturethe mixture heated
  5. temperatureThe mixture was refluxed for another additional 4 hours
  6. distillationThe flashed mixture was then distilled through a 0.7×30 cm

Sources & evidence

ORD record
ord-e9f058684c4544b6aa52e534f9499843
Source dataset
uspto-grants-1984_12
Patent number
USRE031771

Reaction notes

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