Bromobenzene → 7-Phenoxy-1-tetralone

HRID 376894

Reaktionsgleichung

Reaktionsgleichung von HRID 376894
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][C:15]2=[O:18])=[CH:10][CH:9]=1.Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1.[Cu]=O>[O:7]([C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][C:15]2=[O:18])=[CH:10][CH:9]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 3

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-one

Produkt 1

HCID 43187537-Phenoxy-1-tetraloneAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14829Copper oxideKatalysatorHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A suspension of 60.8 g potassium carbonate in 300 ml of dry pyridine was treated with 35.7 g 7-hydroxy-3,4-dihydro-2H-naphthalen-1-one, and the mixture was heated to 40° C. Thereafter, 19.9 g copper(II) oxide was added thereto with stirring, followed by the drop-wise addition of 39.6 g bromobenzene. The reaction mixture was heated for 4 days under reflux. After evaporating the pyridine completely under vacuum, the residue was stirred with 200 ml ethyl acetate and was filtered through silica gel. The filtrate was washed with saturated solutions of ammonium chloride and sodium chloride, dried over sodium sulfate and concentrated by evaporation under vacuum. The residue was purified by column chromatography, using n-hexane/ethyl acetate as the elutant, whereupon 41.2 g (78.6% of theoretical) 7-phenoxy-3,4-dihydro-2H-naphthalen-1-one was obtained.

Aufarbeitung

  1. temperatureThe reaction mixture was heated for 4 days
  2. temperatureunder reflux
  3. customAfter evaporating the pyridine completely under vacuum
  4. stirringthe residue was stirred with 200 ml ethyl acetate
  5. filtrationwas filtered through silica gel
  6. washThe filtrate was washed with saturated solutions of ammonium chloride and sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated by evaporation under vacuum
  9. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0f1870388fd140ee8c997c5a0bd311e2
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06022895

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