Glyoxylic Acid → 4-Hydroxyphenylglycine

HRID 46942

Reaction equation

HRID 46942 reaction equation
[C:1]([OH:5])(=[O:4])[CH:2]=O.C([O-])(=O)C.[NH4+:10].[C:11]1([OH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[CH:13]1[C:14]([CH:2]([NH2:10])[C:1]([OH:5])=[O:4])=[CH:15][CH:16]=[C:11]([OH:17])[CH:12]=1

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 996PhenolHCID 517165Ammonium Acetate

Product 1

HCID 921434-HydroxyphenylglycineYield 28.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 g of an aqueous 40% glyoxylic acid solution are added to 70 ml of water, and 37.5 g of ammonium acetate and 22.5 g of phenol are added thereto under stirring. The mixture is stirred at room temperature for 41 hours. The crystalline precipitates are collected by filtration under cooling, and then successively washed with water and methanol. 7.8 g of DL-p-hydroxyphenylglycine are thereby obtained as white crystals. Yield: 28.9%, M.p. 225°-228° C. (decomp.).

Workup

  1. additionare added
  2. stirringThe mixture is stirred at room temperature for 41 hours
  3. customThe crystalline precipitates
  4. filtrationare collected by filtration
  5. temperatureunder cooling
  6. washsuccessively washed with water and methanol

Sources & evidence

ORD record
ord-4a71fba6378949a183990fe45aff8c26
Source dataset
uspto-grants-1979_11
Patent number
US04175206

Linked notes

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