Water → HCID 18763429, Verbindung

HRID 431385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 431385
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1.O>CC(C)=O>[CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[CH2:22][O:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 239344Methyl 3-hydroxy-5-nitrobenzoate

Produkt 1

HCID 18763429HCID 18763429, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Methyl 3-hydroxy-5-nitrobenzoate (0.685 g, 3.5 mmol) was dissolved in acetone (75 mL). Potassium carbonate (1.43 g, 10.4 mmol) and 2-bromomethylnaphthalene (0.77 g, 3.5 mmol) were added, and the whole was stirred under reflux for 5 h. Mixture was cooled to room temperature and poured into basic (NaOH, pH 10-11) water. After 1 h, precipitated solid was filtered, washed with water (3×25 mL), and air-dried. Off-white crystals, yield 0.970 g (82%). 1H NMR (DMSO-d6, 400 MHz), δ: 8.24 (s, 1H); 8.14 (s, 1H); 8.05 (s, 1H); 7.99-7.90 (m, 4H); 7.63 (d, J=7.5 Hz, 1H); 7.57-7.50 (m, 2H); 5.51 (s, 2H); 3.92 (s, 3H).

Aufarbeitung

  1. temperatureunder reflux for 5 h
  2. customprecipitated solid
  3. filtrationwas filtered
  4. washwashed with water (3×25 mL)
  5. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-3167dc5f560f4a3fb2af119042afd46a
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06656971B2

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