Benzyl Bromide → 2-(2-(Benzyloxy)phenyl)ethanol

HRID 617582

Reaktionsgleichung

Reaktionsgleichung von HRID 617582
[O-]CC.[Na+].[OH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][OH:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[CH2:15]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][OH:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 822002-(2-Hydroxyethyl)phenolHCID 2723922Sodium ethoxide

Produkt 1

HCID 5621842-(2-(Benzyloxy)phenyl)ethanolAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of sodium ethoxide (10.8 g) in ethanol (500 ml), 2-(2-hydroxyphenyl)ethanol (20.0 g) and benzyl bromide (24.8 g) were added and the mixture was refluxed under heating for 2 hours. The solvent was distilled away under reduced pressure, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a 2M aqueous potassium hydroxide solution and a saturated brine and dried over sodium sulfate. The solvent was distilled away under reduced pressure and the residue was subjected to silica gel chromatography (eluent; hexane-ethyl acetate=8:1) to give the subject compound (27.2 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. distillationThe solvent was distilled away under reduced pressure, water
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with a 2M aqueous potassium hydroxide solution
  7. dry with materiala saturated brine and dried over sodium sulfate
  8. distillationThe solvent was distilled away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6a4af131d4c64fa596be22bb28b7d310
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948820

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