Potassium Cyanide → Methyl 3-(cyanomethyl)benzoate

HRID 2225052Notes

Reaction equation

HRID 2225052 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+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[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

5

Reactant 3

HCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 10821136Methyl 3-(cyanomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of methyl 3-(bromomethyl)benzoate (0.6 gram, 2.6 mmol), potassium cyanide (0.35 gram, 5.2 mmol) and 60 mg of 18-crown-6 in 6 ml acetonitrile was vigorously stirred at room temperature for 24 hours. The mixture was filtered, the filtrate concentrated to half volume, water was added to the remaining mixture and extraction was performed with dichloromethane. The organic phase was dried over MgSO4 and the solvent was evaporated, to give the product as a yellow liquid, which was used without purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated to half volume, water
  3. additionwas added to the remaining mixture and extraction
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-973edd7df3d2489487cf26a469efcdf9
Source dataset
uspto-grants-2008_05
Patent number
US07378432B2

Reaction notes

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