Hydroxylamine → 2-Hydroxyimino-2-(3-hydroxyphenyl)acetic acid

HRID 463828Notes

Reaction equation

HRID 463828 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=O)[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[NH2:13][OH:14]>CO>[OH:14][N:13]=[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([OH:1])[CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 135480972-(3-Hydroxyphenyl)-2-oxo-ethanoic acid

Product 1

HCID 867363792-Hydroxyimino-2-(3-hydroxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-Hydroxyphenyl)glyoxylic acid (3.32 g.) and 1N-methanol solution of hydroxylamine (45 ml.) were refluxed with stirring for 25 minutes. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in 1N-aqueous solution of sodium hydroxide (70 ml.). An aqueous solution was washed with ether, acidified with dil. hydrochloric acid and then extracted with ethyl acetate. The extract was washed, dried and treated with an activated charcoal. The solvent was distilled off to give 2-hydroxyimino-2-(3-hydroxyphenyl)acetic acid (a mixture of syn and anti isomers) (2.9 g.).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 1N-aqueous solution of sodium hydroxide (70 ml.)
  3. washAn aqueous solution was washed with ether
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed
  6. customdried
  7. additiontreated with an activated charcoal
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-51dc0ccf26754c149c00475d97a4ae1f
Source dataset
uspto-grants-1985_10
Patent number
US04544653

Reaction notes

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