Methanol → Methyl 5-bromo-1-naphthoate

HRID 1166791

Reaktionsgleichung

Reaktionsgleichung von HRID 1166791
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([OH:14])=[O:13].OS(O)(=O)=O.[CH3:20]O>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([O:14][CH3:20])=[O:13]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6976055-Bromonaphthalene-1-carboxylic acid

Produkt 1

HCID 4557673Methyl 5-bromo-1-naphthoateAusbeute 92 %

Versuchsvorschrift

To a suspension of 5-bromo-1-naphthylcarboxylic acid (5 g, 20 mmol) in 200 mL anhydrous MeOH was added 5 mL concentrated H2SO4 and refluxed overnight. The reaction was cooled to room temperature and concentrated to one-third the volume. The residue was diluted with water and extracted with diethyl ether. The organic layer was separated and washed with water (2×), dried over MgSO4, and concentrated. Silica gel column chromatography using hexane/ethyl acetate (2/11) gave 4.91 g (92%) of the product.

Aufarbeitung

  1. temperaturerefluxed overnight
  2. concentrationconcentrated to one-third the volume
  3. additionThe residue was diluted with water
  4. extractionextracted with diethyl ether
  5. customThe organic layer was separated
  6. washwashed with water (2×)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-aba7faf794b04d7faf03e077913ee7f3
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613942B1

Verknüpfte Notizen

Wird geladen…