Phenol → Phenoxyacetic Acid

HRID 1249654Notes

Reaction equation

HRID 1249654 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:9][C:10]([O:12]CC)=[O:11].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[O:7]([CH2:9][C:10]([OH:12])=[O:11])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 5238Sodium IodideHCID 7751Ethyl chloroacetateHCID 11430Potassium Carbonate

Product 1

HCID 19188Phenoxyacetic AcidYield 60.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Phenol (d5) 4.6 g, ethyl chloroacetate (6.25 g), sodium iodide (7.5 g) and anhydrous potassium carbonate (7 g) were refluxed for 12 hours in dry acetone (50 ml). The mixture was then stirred into a large volume of water and the solution extracted with ether. Unreacted phenol was removed with cold 1N NaOH solution. The ether extract was dried over anhydrous sodium sulphate, filtered and concentrated under vacuum. The residual oil (8.0 g) without further purification, was hydrolyzed by 10% NaOH in D2O affording phenoxyacetic acid (4.5 g).

Workup

  1. extractionthe solution extracted with ether
  2. customwas removed with cold 1N NaOH solution
  3. extractionThe ether extract
  4. dry with materialwas dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residual oil (8.0 g) without further purification

Sources & evidence

ORD record
ord-246067e4cf7140f1acff214b266edcd3
Source dataset
uspto-grants-2002_01
Patent number
US06334997B1

Reaction notes

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