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

HRID 2292860Notes

Reaction equation

HRID 2292860 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]>[Ni].C(O)C>[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 86%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

10 g of 3-(4-hydroxyphenyl)pyruvic acid and 50 ml of ethanol were charged to a pressure reactor to form a solution, and 1.0 g of Raney nickel was added thereto. The atmosphere was displaced with hydrogen, and the mixture was stirred at 70° C. under a hydrogen pressure of 30 kg/cm2 for 0.5 hour. After completion of the reaction, the reaction mixture was filtered to remove the catalyst, and the filtrate was concentrated under reduced pressure to give 8.7 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-ed6a08615aac4e24a316be520c0dc92c
Source dataset
uspto-grants-1997_11
Patent number
US05684186

Reaction notes

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