Reaction #1909816

Reaction equation

water

sodium cyanide

4-tert-butylbenzyl bromide

water

→

4-tert-butylphenylacetonitrile

Yield 31.2%

Solvents

DMSO

Conditions

Workup

1. 1
   workup.STIRRINGthe resulting mixture was further stirred at 50° C. for 5 hours
2. 2
   workup.WAITAfter this was left
3. 3
   Otherto be at room temperature
4. 4
   Extractionextracted with ether
5. 5
   WashThe organic layer was washed with water
6. 6
   Dryingdried over sodium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   OtherThe residual product was purified through silica gel column chromatography

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.

Source