Phenol → Phenoxyacetic Acid

HRID 324913Notes

Reaction equation

HRID 324913 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-10eb7f184fcf48e88d701fdc144c7be0
Source dataset
uspto-grants-2001_04
Patent number
US06221335B1

Reaction notes

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