Benzyl Bromide → 4-Benzyloxyphenylacetonitrile

HRID 2186333Notes

Reaction equation

HRID 2186333 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 95.4%

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-dfcc0847718f40c7b3f5c2e2bc73f8f8
Source dataset
uspto-grants-2002_06
Patent number
US06403632B1

Reaction notes

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