Sodium Hydroxide → 6-Bromo-2-hydroxynaphthalene-1-carboxylic acid

HRID 480450

Reaktionsgleichung

Reaktionsgleichung von HRID 480450
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([CH:12]=[O:13])=[C:7]([OH:14])[CH:6]=[CH:5]2.[O-:15]Cl=O.[Na+].[OH-].[Na+]>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([C:12]([OH:15])=[O:13])=[C:7]([OH:14])[CH:6]=[CH:5]2

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 7354576-Bromo-2-hydroxy-1-naphthaldehydeHCID 23668197Sodium Chlorite2×

Produkt 1

HCID 187690886-Bromo-2-hydroxynaphthalene-1-carboxylic acidAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a ice-cooled mixture of 6-Bromo-2-hydroxy-1-naphthaldehyde (24.0 g) and aqueous NaH2PO4 solution (3.2 g in 30 mL of water) in DMSO (160 mL) was added dropwise a solution of NaClO2 (80%; 15.1 g) in water (150 mL) over 1 h. After being stirred for 5 h at room temperature, a solution of NaClO2 (80%; 2.16 g) in water (20 mL) was added, and the reaction mixture was further stirred for 2 h at room temperature. The mixture was alkalized with 1N-NaOH, and the precipitate was filtered off. The filtrate was washed with AcOEt and iPr2O, and then the aqueous phase was acidified with conc. HCl. The precipitate was filtered, washed with water, and dried in vacuo to give the title compound (22.3 g) as a brown powder.

Aufarbeitung

  1. stirringthe reaction mixture was further stirred for 2 h at room temperature
  2. filtrationthe precipitate was filtered off
  3. washThe filtrate was washed with AcOEt and iPr2O
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-73b91b7fca7a45499716b10d2f9d370b
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06649643B1

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