Thiophenol → 3-Chloropropyl phenyl sulfide

HRID 435109Notes

Reaction equation

HRID 435109 reaction equation
[OH-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:11][CH2:12][CH2:13][Cl:14]>O>[C:3]1([S:9][CH2:11][CH2:12][CH2:13][Cl:14])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide

Product 1

HCID 2696063-Chloropropyl phenyl sulfide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution containing 1.1 mole sodium hydroxide in 500 ml water are added 1 mole thiophenol and 2 moles 1-bromo-3-chloro-propane. The mixture is then refluxed for 30 hours, with vigorous stirring. After cooling, the resulting material is extracted with methylene chloride. After washing with dilute lye, and then with water, the solvent is evaporated in vacuo. The product, 3-phenylthio-1-chloropropane, distills at 138°-140° C. under 13 mm Hg.

Workup

  1. temperatureThe mixture is then refluxed for 30 hours, with vigorous stirring
  2. temperatureAfter cooling
  3. extractionthe resulting material is extracted with methylene chloride
  4. washAfter washing
  5. additionwith dilute lye
  6. customwith water, the solvent is evaporated in vacuo
  7. distillationThe product, 3-phenylthio-1-chloropropane, distills at 138°-140° C. under 13 mm Hg

Sources & evidence

ORD record
ord-dbc0cfafe4d141afbbdab692cb06efe5
Source dataset
uspto-grants-1983_08
Patent number
US04400381

Reaction notes

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