Acetone → (4-Chlorophenoxy)acetic acid

HRID 2069325Notes

Reaction equation

HRID 2069325 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([O:13]C)=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)=O>CC#N.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 60984Methyl bromoacetate

Product 1

HCID 26229(4-Chlorophenoxy)acetic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chlorophenol (500 mg), methyl bromoacetate (0.368 ml), cesium carbonate (1.9 g) and 5 ml of acetone was stirred at room temperature for 12 h. Ethyl acetate and water were then added to the reaction solution, and the organic phase was washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The crude product was dissolved in a 1:1 THF/water mixture (10 ml), and potassium hydroxide (417 mg) was added. The reaction was stirred at room temperature for 12 h. Ethyl acetate and water were then added to the reaction solution, and the aqueous phase was adjusted to pH 2 and extracted several times with ethyl acetate. The combined organic phases were washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The product with the molecular weight of 186.6 (C8H7ClO3) was obtained in this way; MS (ESI): 227.0 (M+CH3CN).

Workup

  1. washthe organic phase was washed twice with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. dissolutionThe crude product was dissolved in a 1:1 THF/water mixture (10 ml), and potassium hydroxide (417 mg)
  6. additionwas added
  7. stirringThe reaction was stirred at room temperature for 12 h
  8. additionEthyl acetate and water were then added to the reaction solution
  9. extractionextracted several times with ethyl acetate
  10. washThe combined organic phases were washed twice with water
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customthe solvent was removed in vacuo
  14. customThe product with the molecular weight of 186.6 (C8H7ClO3) was obtained in this way

Sources & evidence

ORD record
ord-6fd7962e887c457b9f6c4dc5141e5171
Source dataset
uspto-grants-2012_10
Patent number
US08299104B2

Reaction notes

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