Benzyl Bromide → 4-Benzyloxyphenylacetonitrile

HRID 1106655Notes

Reaction equation

HRID 1106655 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-79719caa7a1446dbacaf5502c04cc61f
Source dataset
uspto-grants-2000_05
Patent number
US06057336

Reaction notes

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