Formaldehyde → Glyoxylic Acid

HRID 1195638Notes

Reaction equation

HRID 1195638 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=[O:4].C=O.C(O)(C)C.[P:13](=[O:17])([OH:16])([OH:15])[OH:14]>>[P:13]([O-:17])([OH:16])([OH:15])=[O:14].[C:2]([OH:6])(=[O:5])[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1004Phosphoric AcidHCID 3776IsopropanolHCID 15620607Glyoxylic acid, monohydrate

Product 2

HCID 760Glyoxylic AcidHCID 1003Dihydrogenphosphate

Conditions

Temperature
40 °C

Procedure

29.3 g (0.100 mole) of 4-diazodiphenylamine hydrogensulfate was dissolved in 70 ml of an 85% phosphoric acid solution. Then 4.74 g (0.0500 mole) of glyoxylic acid monohydrate (97%) was added to this solution and the mixture was stirred at 40° C. for 20 hours. Then 1.58 g (0.0500 mole) of paraformaldehyde (95% ) was added to the reaction mixture and the mixture was stirred at 40° C. for additional 20 hours. Thereafter, the reaction solution was poured into 800 ml of isopropyl alcohol while stirring, to form yellow precipitate. The yellow precipitate was obtaided by filtering and washed with isopropyl alcohol, to give dihydrogenphosphate of a condensate of 4-diazodiphenylamine with glyoxylic acid.formaldehyde.

Workup

  1. stirringthe mixture was stirred at 40° C. for additional 20 hours
  2. stirringwhile stirring
  3. customto form yellow precipitate
  4. filtrationby filtering
  5. washwashed with isopropyl alcohol

Sources & evidence

ORD record
ord-4fe90bb0bdd244e4a632a95fe76dee30
Source dataset
uspto-grants-1992_05
Patent number
US05112743

Reaction notes

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