Potassium Hydroxide → 3-(4-Benzyloxyphenyl)propionic acid

HRID 867602Notes

Reaction equation

HRID 867602 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([O:19]CC2C=CC=CC=2)=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14281237HCID 14281237, compound

Product 1

HCID 5613723-(4-Benzyloxyphenyl)propionic acidYield 73.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzyl 3-(4-benzyloxyphenyl)propionate (9.25 g) and a solution of 2.8 g potassium hydroxide in 95% ethanol (125 ml) were placed in a flask, and the mixture was heated under reflux for 30 minutes. At the end of reaction, the solvent was distilled off, ethyl acetate was added to the residue, and the resulting mixture was transferred to a separating funnel. After washing with 1N HCl and water, the ethyl acetate layer was collected and dried over anhydrous sodium sulfate, the solvent was distilled off from the dried solution, and the residue was recrystallized from ethyl acetate/hexane, affording 5 g (72.7%) of pure 3-(4-benzyloxyphenyl)propionic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. customAt the end of reaction
  4. distillationthe solvent was distilled off
  5. additionethyl acetate was added to the residue
  6. customthe resulting mixture was transferred to a separating funnel
  7. washAfter washing with 1N HCl and water
  8. customthe ethyl acetate layer was collected
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off from the dried solution
  11. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ba84f9efd3c142f7803fb62df2f34886
Source dataset
uspto-grants-1988_10
Patent number
US04775743

Reaction notes

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