Potassium Cyanide → Methyl 3-(cyanomethyl)benzoate

HRID 587928Notes

Reaction equation

HRID 587928 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C-:13]#[N:14].[K+]>CO>[C:13]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:14]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 10821136Methyl 3-(cyanomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 5.71 g (24.9 mmol) of methyl 3-bromomethylbenzoate in 36 mL of methanol was added 2.11 g (32.4 mmol) of potassium cyanide. The mixture was refluxed for about 16 h, cooled to 22° C. and filtered. The filtrate was evaporated and the residue was purified by flash chromatography on silica gel, eluting first with hexane and then gradually increasing to 15% ethyl acetate/hexane to give methyl 3-(cyanomethyl)benzoate.

Workup

  1. temperatureThe mixture was refluxed for about 16 h
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe residue was purified by flash chromatography on silica gel
  5. washeluting first with hexane
  6. temperaturegradually increasing to 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6485e11f1b8e4096bab8b27cf60767ad
Source dataset
uspto-grants-2016_01
Patent number
US09227918B2

Reaction notes

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