Phenol → (3-Chloropropoxy)benzene

HRID 1704737Notes

Reaction equation

HRID 1704737 reaction equation
[C:1]1([OH: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>[O:7]([CH2:11][CH2:12][CH2:13][Cl:14])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide2×

Product 1

HCID 76917(3-Chloropropoxy)benzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of phenol (1 mole), sodium hydroxide (1 mole) and 3-bromo-1-chloro-propane (2 moles) in water (1000 ml) and ethyl alcohol (250 ml) is refluxed during 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. It is then dried over sodium sulfate, concentrated in vacuo over a water-bath and the residual oil is distilled. B.p. = 118°-120° C./15 mm Hg.

Workup

  1. temperatureis refluxed during 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 materialIt is then dried over sodium sulfate
  6. concentrationconcentrated in vacuo over a water-bath
  7. distillationthe residual oil is distilled

Sources & evidence

ORD record
ord-107208654e91464396e3a12f949bf433
Source dataset
uspto-grants-1978_11
Patent number
US04127661

Reaction notes

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