Ethanol → m-Phenoxybenzyl cyanide

HRID 1074581Notes

Reaction equation

HRID 1074581 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[C-:19]#[N:20].[Na+]>O>[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][C:19]#[N:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8929Sodium CyanideHCID 932913-Phenoxybenzyl chloride

Product 1

HCID 40075m-Phenoxybenzyl cyanideYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 218 g. m-phenoxy-benzyl chloride in 850 ml. of 96% ethyl alcohol a solution of 57.8 g. of sodium cyanide in 100 ml. of water is added at once. The reaction mixture is boiled under stirring until the starting material cannot be detected anymore by thin layer chromatography. When the reaction is completed the reaction mixture is poured into 1 liter of water and the separating oil is extracted with 3×500 ml. of benzene. The combined benzene solutions are washed with 1 liter of water and dried above sodium sulphate. Sodium sulphate is filtered off and benzene is distilled off. 190 g. (91%) of m-phenoxy-benzyl cyanide are obtained (purity more than 90%, determined by gas chromatography). Boiling point 138° C./0.2 mmHg.

Workup

  1. extractionthe separating oil is extracted with 3×500 ml
  2. washThe combined benzene solutions are washed with 1 liter of water
  3. dry with materialdried above sodium sulphate
  4. filtrationSodium sulphate is filtered off
  5. distillationbenzene is distilled off

Sources & evidence

ORD record
ord-7b1804dc6b2141949536688554f8d12d
Source dataset
uspto-grants-1983_07
Patent number
US04393008

Reaction notes

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