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

HRID 1272041
ノート
印刷プレビュー

反応式

HRID 1272041 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-cb94d74628024c14acb41a79151531ba
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07208497B2

反応ノート

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