3,4-Dihydroxyphenylpyruvic acid → 3-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acid

HRID 909280Notes

Reaction equation

HRID 909280 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](=[O:14])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8]>Cl>[OH:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([OH:14])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

3

Reactant 1

HCID 1651983,4-Dihydroxyphenylpyruvic acid

Product 1

HCID 4394353-(3,4-Dihydroxyphenyl)-2-hydroxypropanoic acidYield 40.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Into 0.17 mol β-(3,4-dihydroxylphenyl)pyruvic acid, 112 g zinc amalgam and 1808 mL of 1.4 mol·L−1 hydrochloric acid solution were added, and the reaction was performed under heating and refluxing for 8 h. After filtration, the filtrate was extracted using ethyl acetate repeatedly, dried using anhydrous Na2SO4. After removal of ethyl acetate, β-(3,4-dihydroxylphenyl)-α-hydroxylpropionic acid was obtained in a yield of 40.3%.

Workup

  1. temperatureunder heating
  2. temperaturerefluxing for 8 h
  3. filtrationAfter filtration
  4. extractionthe filtrate was extracted
  5. customdried
  6. customAfter removal of ethyl acetate

Sources & evidence

ORD record
ord-613dab07193043298dba9fea50ff9970
Source dataset
uspto-grants-2011_09
Patent number
US08017786B2

Reaction notes

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