Potassium Hydroxide → 2-Methylene-4-phenylbutyric acid

HRID 1780022Notes

Reaction equation

HRID 1780022 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](=[CH2:15])[C:10]([O:12]CC)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C(O)C>[CH2:15]=[C:9]([CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11117162Ethyl alpha-(phenethyl)acrylate

Product 1

HCID 138174112-Methylene-4-phenylbutyric acidYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Phenyl-2-methylenebutyric acid, ethyl ester (10 g, 49 mmole) was dissolved in 100 mL of absolute ethanol. Potassium hydroxide (3.32 g, 85%, 50 mmole) was added to the solution and the solution stirred overnight at room temperature. After 18 h, all of the ester was hydrolyzed. The solvent was removed under reduced pressure and the syrup dissolved in water. Enough concentrated HCl was added to acidify the solution (pH<3) and the product was extracted with ether (3×50 mL). The solution was dried over MgSO4, filtered and the solvent removed under reduced pressure. Recovered 8.6 g of product (97% yield).

Workup

  1. waitAfter 18 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe syrup dissolved in water
  4. additionEnough concentrated HCl was added
  5. extractionthe product was extracted with ether (3×50 mL)
  6. dry with materialThe solution was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4e5603af682343138b8101879d09ddb5
Source dataset
uspto-grants-1997_05
Patent number
US05629343

Reaction notes

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