Potassium Cyanide → Methyl 3-(cyanomethyl)benzoate

HRID 1663650Notes

Reaction equation

HRID 1663650 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+]>C(#N)C.C1OCCOCCOCCOCCOCCOC1>[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 2

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

Product 1

HCID 10821136Methyl 3-(cyanomethyl)benzoateYield 91%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 3-(bromomethyl)benzoate (10.0 g, 44 mmol) in acetonitrile (100 mL) were added potassium cyanide (5.7 g, 87 mmol) and 18-crown-6 (1.0 g), and the mixture was stirred at room temperature for 3 days. The reaction mixture was filtrated, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→30/70). The combined solution was concentrated under reduced pressure to give the title compound (7.0 g, 91%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtrated
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=5/95→30/70)
  4. concentrationThe combined solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9d69c4c6765f48f1bc0af1fed53c44a0
Source dataset
uspto-grants-2011_10
Patent number
US08034812B2

Reaction notes

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