(R)-2-acetoxy-4-oxo-4-phenylbutyric acid → (R)-2-Hydroxy-4-phenylbutyric acid

HRID 1384498Notes

Reaction equation

HRID 1384498 reaction equation
C([O:4][C@H:5]([CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7])(=O)C.[H][H]>C(O)(=O)C.[Pd]>[OH:4][C@H:5]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

5

Reactant 2

HCID 10944423(R)-2-acetoxy-4-oxo-4-phenylbutyric acidHCID 178418361HCID 178418361, compound

Product 1

HCID 2759328(R)-2-Hydroxy-4-phenylbutyric acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(R)-2-acetoxy-4-oxo-4-phenylbutyric acid (2.36 g) was dissolved in 15 ml of acetic acid, and 0.21 g of 5% by weight palladium on carbon (water content 50%) were added thereto. The mixture was stirred in a hydrogen atmosphere at 60° C. for 24 hours. Palladium on carbon was separated by filtration, and the solvent was then distilled off. Thirty milliliters of 1−N hydrochloric acid were added to the resulting (R)-2-acetoxy-4-phenylbutyric acid, and the mixture was heat-refluxed for 3 hours while being stirred.

Workup

  1. customPalladium on carbon was separated by filtration
  2. distillationthe solvent was then distilled off
  3. additionThirty milliliters of 1−N hydrochloric acid were added to the resulting (R)-2-acetoxy-4-phenylbutyric acid
  4. temperaturethe mixture was heat-refluxed for 3 hours

Sources & evidence

ORD record
ord-73a1d342a105402b9441be63ff72c914
Source dataset
uspto-grants-2001_07
Patent number
US06258975B1

Reaction notes

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