Acetic Acid → 4-(3,4-Dichlorophenyl)-2-hydroxy-4-oxobutanoic acid

HRID 1272041Notes

Reaction equation

HRID 1272041 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([Cl:11])[CH:5]=1)=[O:3].C(O)(=O)C.O.[C:17]([OH:21])(=[O:20])[CH:18]=[O:19]>O>[Cl:11][C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH2:1][CH:18]([OH:19])[C:17]([OH:21])=[O:20])[CH:9]=[CH:8][C:7]=1[Cl:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 15620607Glyoxylic acid, monohydrate2×

Product 1

HCID 30672544-(3,4-Dichlorophenyl)-2-hydroxy-4-oxobutanoic acidYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3,4-dichloroacetophenone (3.84 g, 20.3 mmol), glacial acetic acid (20.0 ml), and glyoxylic acid hydrate (1.85 g, 20.1 mmol) was stirred at 90° C. for 23 hours. More glyoxylic acid hydrate (0.93 g) was added, and heating was continued for 41 hours. Water (200 ml) was added, and the mixture was extracted twice with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), and concentrated under reduced pressure. Recrystallization of the residue from ethyl acetate/heptane yielded 2.01 g (38%) of 4-(3,4-dichlorophenyl)-4-oxo-2-hydroxybutyric acid. This acid was used to prepare the title amide using General Procedure (D).

Workup

  1. temperatureheating
  2. waitwas continued for 41 hours
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallization of the residue from ethyl acetate/heptane

Sources & evidence

ORD record
ord-cb94d74628024c14acb41a79151531ba
Source dataset
uspto-grants-2007_04
Patent number
US07208497B2

Reaction notes

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