Acetic Acid → HCID 86734657, compound

HRID 328689Notes

Reaction equation

HRID 328689 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=O)C=O.[C:8]([OH:11])(=O)[CH3:9].Cl.C[NH:14][OH:15].O.O.O.C([O-])(=O)C.[Na+]>CO>[CH2:6]([O:5][CH:1]=[N+:14]([CH:9]=[C:8]=[O:11])[O-:15])[CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 70211Ethyl oxoacetateHCID 77906N-methylhydroxylamine hydrochlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 86734657HCID 86734657, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above mixture of ethyl glyoxylate and acetic acid (11.34 g, containing 70 mmol aldehyde) is dissolved in methanol (110 ml), N-methylhydroxylamine hydrochloride (5.8 g) and sodium acetate trihydrate (10.9 g) are added and the mixture is stirred at room temperature for 24 hours. It is then concentrated in vacuo, diluted with water and extracted with dichloromethane. The dichloromethane solution is then washed with a dilute sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate, evaporated and distilled to afford α-ethoxy-carbonyl-N-methyl nitrone as a colorless solid (5.0 g), boiling point 80°-85° C/0.4 mm of Hg., melting point 43°-49° C. This is a mixture of the syn- and anti-isomers on the basis of the nmr spectrum.

Workup

  1. concentrationIt is then concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with dichloromethane
  4. washThe dichloromethane solution is then washed with a dilute sodium bicarbonate solution and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. distillationdistilled

Sources & evidence

ORD record
ord-65f28756623143b6a25d15b17258ba4c
Source dataset
uspto-grants-1977_04
Patent number
US04018774

Reaction notes

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