Sodium Cyanide → Ethyl 3-(cyanomethyl)benzoate

HRID 1257447Notes

Reaction equation

HRID 1257447 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[C-:14]#[N:15].[Na+]>CSC.O>[C:14]([CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:15]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 14812190Ethyl 3-(chloromethyl)benzoate

Product 1

HCID 83311Ethyl 3-(cyanomethyl)benzoateYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1068Dimethyl SulfideSolvent

Procedure

To a solution of ethyl 3-(chloromethyl)benzoate (5.0 g, 25.1 mmol) in dimethylsulfide (50 mL) was added sodium cyanide (1.85 g, 37.8 mmol), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, and the extract was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (4.23 g, 89%) as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed successively with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-78727aa4f47b4393904f5fa9b1850504
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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