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

HRID 2285840Notes

Reaction equation

HRID 2285840 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 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-ffd76ed5c5c4499b9553f40dd895d3d7
Source dataset
uspto-grants-1982_04
Patent number
US04324920

Reaction notes

Loading…