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

HRID 2292861Notes

Reaction equation

HRID 2292861 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].O1CCOCC1>[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 98.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

10 g of 3-(4-hydroxyphenyl)pyruvic acid and 50 ml of dioxane 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 70° C. under a hydrogen pressure of 5 kg/cm2 for 6 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 10.0 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-427af5ca1afd438893d3fd5c3688033f
Source dataset
uspto-grants-1997_11
Patent number
US05684186

Reaction notes

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