2,6-Dimethylthiophenol → 2-[(2,6-Dimethylphenyl)sulfanyl]ethan-1-ol

HRID 1389771Notes

Reaction equation

HRID 1389771 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[SH:9].Cl[CH:11]([OH:13])[CH3:12]>[OH-].[Na+].O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[S:9][CH2:12][CH2:11][OH:13]

Participants

5

Reactant 2

HCID 610452,6-DimethylthiophenolHCID 126390351-Chloroethan-1-ol

Product 1

HCID 27586362-[(2,6-Dimethylphenyl)sulfanyl]ethan-1-olYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

35 g. 2,6-dimethyl thiophenol are dissolved in a solution of 15.6 g sodium hydroxide in 210 ml water, under stirring and inert atmospher. After complete dissolution 34 g chloro ethanol are added portionwise thereto and the milky suspension is thereafter heated to reflux for one hour. The mixture reverts to room temperature and is extracted three times with ester to isolate the thus formed oily product. The ethereous solutions are washed with water, dried on sodium sulphate, filtered and evaporated off. 2-(2,6-dimethyl phenylthio) 1-hydroxy ethane is obtained with a yield of 95%. It is further used for the next step without any purification

Workup

  1. additionare added portionwise
  2. temperaturethe milky suspension is thereafter heated
  3. temperatureto reflux for one hour
  4. customreverts to room temperature
  5. extractionis extracted three times with ester
  6. customto isolate the thus formed oily product
  7. washThe ethereous solutions are washed with water
  8. customdried on sodium sulphate
  9. filtrationfiltered
  10. customevaporated off

Sources & evidence

ORD record
ord-059ad6b88140418dbc6aec51b76a43c2
Source dataset
uspto-grants-1981_01
Patent number
US04246267

Reaction notes

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