Potassium Hydroxide → 3-Hydroxy-3-phenylpropanoic acid

HRID 1414753Notes

Reaction equation

HRID 1414753 reaction equation
[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6]CC)=[O:5].[OH-].[K+]>C(O)C>[OH:1][CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 99818Ethyl 3-phenylhydracrylate, (+-)-

Product 1

HCID 929593-Hydroxy-3-phenylpropanoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-hydroxy-3-phenylpropanoate (19 g, 0.1 mole) was refluxed in a solution of KOH (10 g, 0.2 mole) in ethanol for two hours. The solvent was removed in vacuo and the residue was dissolved in H2O. The H2O solution was extracted with ethyl ether, then acidified with 37% hydrochloric acid. The oily product was extracted out with chloroform and the chloroform was removed in vacuo to yield 10 g (62.5%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in H2O
  3. extractionThe H2O solution was extracted with ethyl ether
  4. extractionThe oily product was extracted out with chloroform
  5. customthe chloroform was removed in vacuo
  6. customto yield 10 g (62.5%)

Sources & evidence

ORD record
ord-cdcbffa4f09742e9845325766a34354c
Source dataset
uspto-grants-1977_01
Patent number
US04002660

Reaction notes

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