Benzyl Bromide → 4-Benzyloxyphenylacetonitrile

HRID 398025

Reaktionsgleichung

Reaktionsgleichung von HRID 398025
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[CH2:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanide

Produkt 1

HCID 5228044-BenzyloxyphenylacetonitrileAusbeute 358,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Hydroxybenzyl cyanide (2.5 g, 18.77 mmol), benzyl bromide (3.8 g, 22:5 mmol) and potassium carbonate (45 mmol) were combined in acetone (50 mL) and heated to reflux for 8 h. The reaction was allowed to cool to rt, diluted with ethyl acetate and filtered to remove the solids. The organic layer was concentrated in vacuo to give an oil. The crude benzyl ether was purified by chromatography on silica gel eluting hexane:ethyl acetate (90:10, v:v) to give 4-benzyloxybenzyl cyanide (4.0 g, 95%) which solidified. MS (M+NH4)+=241.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 8 h
  3. filtrationfiltered
  4. customto remove the solids
  5. concentrationThe organic layer was concentrated in vacuo
  6. customto give an oil
  7. customThe crude benzyl ether was purified by chromatography on silica gel
  8. washeluting hexane:ethyl acetate (90:10, v:v)

Quellen und Nachweise

ORD-Eintrag
ord-bc2d91ce438746bbbad4db8247c636a0
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610731B2

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