4-Hydroxyphenylpyruvic Acid → (+-)-3-(4-Hydroxyphenyl)lactic acid

HRID 2292857Notes

Reaction equation

HRID 2292857 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:13])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[H][H]>[Pd].CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([OH:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 9794-Hydroxyphenylpyruvic AcidHCID 178418361HCID 178418361, compound

Product 1

HCID 9378(+-)-3-(4-Hydroxyphenyl)lactic acidYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

10 g of 3-(4-hydroxyphenyl)pyruvic acid and 50 ml of methanol were charged to a pressure reactor to form a solution, and 0.5 g of 5% palladium on charcoal was added thereto. The atmosphere was displaced with hydrogen, and the mixture was stirred at 25° C. under a hydrogen pressure of 5 kg/cm2 for 2 hours. After completion of the reaction, the reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure to give 10.1 g of 3-(4-hydroxyphenyl)lactic acid as colorless crystals.

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. customto remove the catalyst
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-afb4e72a06444920a5c09666d73da2cc
Source dataset
uspto-grants-1997_11
Patent number
US05684186

Reaction notes

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