Thiophenol → 3-Chloropropyl phenyl sulfide

HRID 1704739Notes

Reaction equation

HRID 1704739 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Br[CH2:11][CH2:12][CH2:13][Cl:14]>O.C(O)C>[C:1]1([S:7][CH2:11][CH2:12][CH2:13][Cl:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide2×

Product 1

HCID 2696063-Chloropropyl phenyl sulfide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of thiophenol (1 mole), sodium hydroxide (1 mole) and 3-bromo-1-chloro-propane (2 moles) in water (1000 ml) and ethanol (250 ml) is refluxed duting 20 hours, with stirring. After cooling, sodium hydroxide (30 g) is added to the reaction medium which is then extracted with methylene chloride. The organic phase is washed with water to neutral pH, after which it is dried over sodium sulfate, concentrated and distilled. B.p. = 165° C./15 mm Hg. N.M.R.: consistent.

Workup

  1. temperatureis refluxed duting 20 hours
  2. temperatureAfter cooling
  3. extractionis then extracted with methylene chloride
  4. washThe organic phase is washed with water to neutral pH
  5. dry with materialafter which it is dried over sodium sulfate
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-c37c9bc206d84c8fad006583cb8ffa0e
Source dataset
uspto-grants-1978_11
Patent number
US04127661

Reaction notes

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