Hydrochloric Acid → 4-Nitrophenylglyoxylic acid

HRID 977066Notes

Reaction equation

HRID 977066 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:18])[C:13]([O:15]CC)=[O:14])=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl>CO>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:12](=[O:18])[C:13]([OH:15])=[O:14])=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 522372Ethyl 4-nitrophenylglyoxylate

Product 1

HCID 1519404-Nitrophenylglyoxylic acidYield 140.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3 ml (6 mmol) of a 2N aqueous solution of sodium hydroxide were added to a solution of 651 mg (2.92 mmol) of ethyl 4-nitrophenylglyoxylate in methanol, and the resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into 2N hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off, to give 0.8 g (quantitative yield) of 4-nitrophenylglyoxylic acid as a crude product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-587bf9f0a6bd441ab99c77d1234c0af4
Source dataset
uspto-grants-1997_03
Patent number
US05614470

Reaction notes

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