Benzyl Bromide → 4-Benzyloxyphenylacetonitrile

HRID 1874311Notes

Reaction equation

HRID 1874311 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanide

Product 1

HCID 5228044-BenzyloxyphenylacetonitrileYield 77.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
56.5 °C

Procedure

Acetone (500 ml) and potassium carbonate (154 g) were charged into RB flask followed by addition of p-hydroxy phenyl acetonitrile (100 g) under stirring. Benzyl bromide (154 g) was then added at ambient temperature, subsequently heating the reaction mass to 55-58° C. and maintaining for 2 hours. The reaction mass was then cooled to 25° C., filtered and washed with acetone (100 ml) to give 130 g (77.8%) of the p-benzyloxyphenyl acetonitrile.

Workup

  1. temperaturemaintaining for 2 hours
  2. temperatureThe reaction mass was then cooled to 25° C.
  3. filtrationfiltered
  4. washwashed with acetone (100 ml)

Sources & evidence

ORD record
ord-62e7be9475384d7b9a34de7c77006b95
Source dataset
uspto-grants-2012_11
Patent number
US08304578B2

Reaction notes

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