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Water → 3-Chloro-4-nitrobenzoic acid

HRID 1773574
ノート
印刷プレビュー

反応式

HRID 1773574 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Mn]([O-])(=O)(=O)=[O:13].[K+].[OH2:18]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[C:8]([OH:13])=[O:18]
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 962WaterHCID 1234783-Chloro-4-nitrotolueneHCID 516875Potassium Permanganate3 回

生成物 1

HCID 5209533-Chloro-4-nitrobenzoic acid収率 84%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
90 °C

実験手順

2-Chloro-4-methyl-1-nitro-benzene (1.2 g, 6.99 mmol) in a mixture of water and pyridine (2/1, 30 mL) was heated at 90° C. then potassium permanganate (5.2 g, 32.9 mmol) was added in 4 portions at intervals of 1.5 hours. The reaction mixture was heated at 90° C. for 8 hours and then more potassium permanganate (2 g) was added and the resulting mixture was stirred at 90° C. overnight. More potassium permanganate (2 g) was added and the resulting mixture was stirred at 90° C. for 1 hour, the solid was filtered off on a CELITE™ pad. Water (50 mL) was added to the filtrate; the resulting mixture was acidified until pH<2 and was extracted 3 times with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 1.19 g (84% yield) of 3-chloro-4-nitro-benzoic acid as a light yellow solid without further purifications

後処理

  1. temperatureThe reaction mixture was heated at 90° C. for 8 hours
  2. stirringthe resulting mixture was stirred at 90° C. for 1 hour
  3. filtrationthe solid was filtered off on a CELITE™ pad
  4. additionWater (50 mL) was added to the filtrate
  5. extractionwas extracted 3 times with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-2cd34dfb78a7405ca5031de6dfd20d5d
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09255110B2

反応ノート

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