Water → (4-tert-Butylphenyl)acetonitrile

HRID 990733Notes

Reaction equation

HRID 990733 reaction equation
[C-:1]#[N:2].[Na+].[C:4]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5].O>CS(C)=O.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>[C:4]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12][C:1]#[N:2])=[CH:10][CH:9]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 962Water2×HCID 8929Sodium CyanideHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

Product 1

HCID 76784(4-tert-Butylphenyl)acetonitrileYield 31.2%

Reagents, catalysts & solvents 2

HCID 26541Dibenzo-18-crown-6CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

0.22 g of dibenzo-18-crown-6-ether and 1.57 g of sodium cyanide were suspended in 20 ml of DMSO, and 5.00 g of 4-tert-butylbenzyl bromide was dropwise added thereto with cooling with water. After having been stirred overnight at room temperature, the resulting mixture was further stirred at 50° C. for 5 hours. After this was left to be at room temperature, water was added thereto and extracted with ether. The organic layer was washed with water, and dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residual product was purified through silica gel column chromatography to obtain 1.19 g of 4-tert-butylphenylacetonitrile was obtained from the fraction eluted with n-hexane:ethyl acetate=5:1.

Workup

  1. stirringthe resulting mixture was further stirred at 50° C. for 5 hours
  2. waitAfter this was left
  3. customto be at room temperature
  4. extractionextracted with ether
  5. washThe organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residual product was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-5622adac819a417ab532cd43b6762348
Source dataset
uspto-grants-2002_10
Patent number
US06462049B1

Reaction notes

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