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

HRID 643948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643948
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-37dc3b88650a4291b8e4aa7937931c57
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700633B2

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