Hydrochloric Acid → 1-(5-Bromo-2-hydroxyphenyl)propan-1-one

HRID 1408729

Reaktionsgleichung

Reaktionsgleichung von HRID 1408729
C([O:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)(=O)CC.[Cl-].[Al+3].[Cl-].[Cl-].Cl>>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([OH:5])=[C:7]([C:6](=[O:5])[CH2:7][CH3:8])[CH:8]=1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 90205p-Bromophenyl propionateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 7364091-(5-Bromo-2-hydroxyphenyl)propan-1-one

Versuchsvorschrift

4-Bromophenyl propionate (34 g, 0.15 mmol) and aluminum chloride (44 g, 0.3 mmol) were heated together at 100° C. for 30 mins. The solution became dark and hydrogen chloride gas was evolved. After cooling, the reaction mixture was carefully poured into ice water, and the resulting mixture was extracted with dichloromethane. The organic layer was washed with brine, dried and concentrated to give the residue, which was purified by column chromatography to give 1-(5-bromo-2-hydroxyphenyl)propan-1-one. (20 g, 59%) 1H NMR (CDCl3, 400 MHz): 1.24 (t, 3H), 2.98-3.04 (m, 2H), 6.88 (d, 1H), 7.52 (t, 1H), 7.76 (s, 1H).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe resulting mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give the residue, which
  7. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8cd35c307ca0492498c56ba1c00b9bef
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921359B2

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