Nitric Acid → 4-Benzyloxy-2-hydroxy-5-nitrobenzaldehyde

HRID 643948ノート

反応式

HRID 643948 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:18]([O-])([OH:20])=[O:19].O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[C:16]([N+:18]([O-:20])=[O:19])=[CH:15][C:12]([CH:13]=[O:14])=[C:11]([OH:17])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 944Nitric AcidHCID 962WaterHCID 5612354-Benzyloxy-2-hydroxybenzaldehyde

生成物 1

HCID 866240244-Benzyloxy-2-hydroxy-5-nitrobenzaldehyde

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a solution of 4-benzyloxy-2-hydroxybenzaldehyde (0.5 g, 2.2 mmol) in 4.4 mL of acetic acid, at 0° C., is added nitric acid (0.28 mL, 4.4 mmol) dropwise. The mixture is stirred at ambient temperature for 18 h. The mixture is poured into water and extracted with EtOAc. The organic layer is washed with water, sat. NaCl and dried over sodium sulfate. The solvent is removed under reduced pressure and the crude material is purified by flash chromatography using hexane/EtOAc (6:1) to afford 4-benzyloxy-2-hydroxy-5-nitrobenzaldehyde as a yellow solid: 1H NMR (acetone-d6) δ 11.84 (s, 1H), 10.08 (s, 1H), 8.59 (s, 1H), 7.64-7.45 (m, 5H), 6.99 (s, 1H), 5.54 (s, 2H); (M−H)−=272.

後処理

  1. extractionextracted with EtOAc
  2. washThe organic layer is washed with water, sat. NaCl
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe crude material is purified by flash chromatography

出典と根拠

ORDレコード
ord-37dc3b88650a4291b8e4aa7937931c57
出典データセット
uspto-grants-2010_04
特許番号
US07700633B2

反応ノート

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