Hydrochloric Acid → 3-(3-Methoxyphenyl)-2-oxopropanoic acid

HRID 27215

Reaction equation

HRID 27215 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.C(N[CH2:15][C:16]([OH:18])=[O:17])(=O)C.C([O-])(=[O:21])C.[Na+].Cl>C(OC(=O)C)(=O)C.O>[CH3:9][O:8][C:4]1[CH:3]=[C:2]([CH2:1][C:15](=[O:21])[C:16]([OH:18])=[O:17])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10972AcetylglycineHCID 115693-MethoxybenzaldehydeHCID 517045Sodium Acetate

Product 1

HCID 2900913-(3-Methoxyphenyl)-2-oxopropanoic acidYield 34.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

m-Anisaldehyde (25.9 g), N-acetylglycine (15.2 g) and sodium acetate (7.8 g) were heated together under reflux in acetic anhydride (50 ml) for 3/4 hour. The mixture was allowed to cool, water (150 ml) was added and the mixture was filtered to give the crude azlactone (27.7 g) m.p. 145°-150°. Hydrolysis with boiling 1 N hydrochloric acid (450 ml) followed by cooling and ether extraction afforded 3-methoxyphenylpyruvic acid as a pale yellow oily solid (6.3 g).

Workup

  1. temperatureto cool
  2. filtrationthe mixture was filtered
  3. customto give the crude azlactone (27.7 g) m.p. 145°-150°
  4. customHydrolysis
  5. temperatureby cooling
  6. extractionether extraction

Sources & evidence

ORD record
ord-0d710401d4e548719286207680e38f38
Source dataset
uspto-grants-1980_09
Patent number
US04220767

Linked notes

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