Sodium Cyanide → (4-tert-Butylphenyl)acetonitrile

HRID 1462150Notes

Reaction equation

HRID 1462150 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:13]([N+:17](CCCC)(CCCC)CCCC)CCC.[C-]#N.[Na+]>O>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][C:13]#[N:17])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 16028TetrabutylammoniumHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

Product 1

HCID 76784(4-tert-Butylphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture consisting of 107 g p-tert.butylbenzyl bromide, 2 g tetra butyl-ammonium jodide and 37 g NaCN in 50 ml water was heated during 1 hour at 100° C. After cooling the reaction mixture, the organic layer was separated and distilled in vacuo with a yield of 78 g of the desired cyanide. Then this product was fractionated in vacuo. Yield of p-tert.butylbenzyl cyanide: 65 g (80%): boiling point: 118° C./0,7 kPa: nD =1,5110. This cyanide has a very strong odor which reminds one of algae, seaweed and ozone with ambergris-like, fatty and animal notes.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customthe organic layer was separated
  3. distillationdistilled in vacuo with a yield of 78 g of the desired cyanide

Sources & evidence

ORD record
ord-af5034d7c5a44ebc89bd5ca9c40ceed5
Source dataset
uspto-grants-1984_07
Patent number
US04459224

Reaction notes

Loading…