Potassium Hydroxide → 3-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid

HRID 2049819Notes

Reaction equation

HRID 2049819 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH:7]2[CH:9]([C:10]([O:12]CC)=[O:11])[C:8]2([CH3:16])[CH3:15])=[CH:4][CH:3]=1.[OH-].[K+]>O.C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH:9]([C:10]([OH:12])=[O:11])[C:8]2([CH3:15])[CH3:16])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 20344552Ethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate

Product 1

HCID 203049613-(4-Chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The ethyl 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylate (l.5 g) is hydrolyzed by heating under reflux with 10% potassium hydroxide in a mixture of 20% water and 80% ethyl alcohol for 1 hr and letting stand at 25° overnight. The solution is cooled and solvent is removed in vacuo. The residue is diluted with water and extracted with ether. The aqueous phase is then acidified with aqueous HCl and extracted with ether. The organic phase is washed with water and brine, dried over sodium sulfate and the solvent removed in vacuo to give 3-(4-chlorophenoxy)-2,2-dimethylcyclopropanecarboxylic acid.

Workup

  1. temperatureby heating
  2. customat 25°
  3. customovernight
  4. temperatureThe solution is cooled
  5. customsolvent is removed in vacuo
  6. additionThe residue is diluted with water
  7. extractionextracted with ether
  8. extractionextracted with ether
  9. washThe organic phase is washed with water and brine
  10. dry with materialdried over sodium sulfate
  11. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5310d75bd8364f5e910f78e7533fafaa
Source dataset
uspto-grants-1980_04
Patent number
US04198527

Reaction notes

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