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

HRID 1272041
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HRID 1272041 반응식
[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]
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참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 15620607Glyoxylic acid, monohydrate2회

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cb94d74628024c14acb41a79151531ba
출처 데이터셋
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07208497B2

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