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

HRID 643948노트

반응식

HRID 643948 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-37dc3b88650a4291b8e4aa7937931c57
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700633B2

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