Benzyl Bromide → 4-Benzyloxyphenylacetonitrile

HRID 398025

Reaction equation

HRID 398025 reaction equation
[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

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanide

Product 1

HCID 5228044-BenzyloxyphenylacetonitrileYield 358.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-bc2d91ce438746bbbad4db8247c636a0
Source dataset
uspto-grants-2003_08
Patent number
US06610731B2

Linked notes

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