Potassium Hydroxide → 2-Methylene-4-phenylbutyric acid

HRID 983673Notes

Reaction equation

HRID 983673 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 hours, all of the ester was hydolyzed. 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 hours
  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-795fb8fb33a4484b906b586ca78a6435
Source dataset
uspto-grants-2005_03
Patent number
US06864383B2

Reaction notes

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