Glyoxylic acid, monohydrate → (Dimethylphosphoryl)(hydroxy)acetic acid

HRID 1981834Notes

Reaction equation

HRID 1981834 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=[O:4].[CH3:7][PH:8](=[O:10])[CH3:9]>C(OCC)(=O)C>[CH3:7][P:8]([CH3:9])([CH:3]([OH:4])[C:2]([OH:6])=[O:5])=[O:10]

Participants

4

Reactant 2

HCID 15620607Glyoxylic acid, monohydrateHCID 178503022methylphosphonoylmethane

Product 1

HCID 119559(Dimethylphosphoryl)(hydroxy)acetic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
25 °C

Procedure

14.8 g (0.2 mol) of glyoxylic acid hydrate in 80 ml of ethyl acetate are added dropwise to a solution of 15.6 g (0.2 mol) of dimethylphosphine oxide in 80 ml of ethyl acetate. During this addition, the temperature rises slightly. The mixture is stirred at 25° C. for 24 hours and the product is filtered off with suction and washed with a little ethyl acetate to give, after drying, 20.2 g (66.5%) of the desired product of melting point 206°-208°.

Workup

  1. additionDuring this addition
  2. filtrationthe product is filtered off with suction
  3. washwashed with a little ethyl acetate
  4. customto give
  5. customafter drying

Sources & evidence

ORD record
ord-a9b9e7d7999341f89278554d4d4ebd49
Source dataset
uspto-grants-1986_06
Patent number
US04594098

Reaction notes

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