Potassium Cyanide → Methyl 3-(cyanomethyl)benzoate

HRID 1360357Notes

Reaction equation

HRID 1360357 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

To methyl 3-bromomethyl-benzoate (25.28 g, 0.11 mol) in acetonitrile (230 mL) is added potassium cyanide (14.3 g, 0.22 mmol) and 18-crown-6 (1.00 g, 2.6 mmol) and the mixture is heated to reflux for 24 h. After filtration, the crude product is transferred to the next step without any further purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 24 h
  3. filtrationAfter filtration
  4. customthe crude product is transferred to the next step without any further purification

Sources & evidence

ORD record
ord-f207549584a6427fa625fe3084742a23
Source dataset
uspto-grants-2011_02
Patent number
US07879853B2

Reaction notes

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