Nitric Acid → 4-(4-Methoxycarbonylphenyl)-2-nitrophenol

HRID 369540

反応式

HRID 369540 の反応式
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)=[O:8].O>C(O)(=O)C>[CH3:5][O:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([N+:1]([O-:4])=[O:2])[CH:16]=2)=[CH:11][CH:10]=1)=[O:8]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 962WaterHCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylate

生成物 1

HCID 185210364-(4-Methoxycarbonylphenyl)-2-nitrophenol収率 93%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Concentrated nitric acid (1.8 ml) was carefully added to a cooled suspension (5-10° C.) of phenol 27 (2.0 mg, 8.8 mmol) in 60 ml of glacial acetic acid. The reaction mixture was stirred for one hour and was then allowed to warm to room temperature and stirred for an additional 30 minutes. Water was added (50 ml) and the reaction mixture was cooled, filtered, and washed with water to yield a yellow powder. The crude product was purified via flash chromatography through a small pad of silica gel with elutions of 80/20 and 50/50 (Hex/EtOAc), respectively. Evaporation of the solvent yielded 2.23 g (93%) of a bright yellow solid.

後処理

  1. stirringstirred for an additional 30 minutes
  2. temperaturethe reaction mixture was cooled
  3. filtrationfiltered
  4. washwashed with water
  5. customto yield a yellow powder
  6. customThe crude product was purified via flash chromatography through a small pad of silica gel with elutions of 80/20 and 50/50 (Hex/EtOAc)
  7. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-368f7166a65c4b70b0aa43e96c7b2b52
出典データセット
uspto-grants-2000_10
特許番号
US06139771

関連ノート

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