Sodium Cyanide → Ethyl 3-(cyanomethyl)benzoate

HRID 1257447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257447
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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 83311Ethyl 3-(cyanomethyl)benzoateAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1068Dimethyl SulfideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-78727aa4f47b4393904f5fa9b1850504
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461348B2

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