Water → Benzoylacetonitrile

HRID 604481Notes

Reaction equation

HRID 604481 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[C:15](#[N:17])[CH3:16].O>CO.C(OCC)C>[O:9]=[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:16][C:15]#[N:17]

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 7165Ethyl benzoateHCID 10942334Sodium Methoxide

Product 1

HCID 64799Benzoylacetonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl benzoate (20 g, 133 mmol) and NaOMe (133 mmol, from 3 g Na) in methanol was mixed and heated with stirring to 80° C. until a homogeneous gelatinous mass had formed. Acetonitrile (6.8 g, 165 mmol) was then added slowly under the surface of this mass over a period of 30 min. The temperature was raised to 120° C. and heated at reflux for 24 h, and the reaction mixture was then cooled on an ice bath and treated with water and diethyl ether until the solid material had dissolved. The aqueous layer was separated and acidified with 5% H2SO4, washed with NaHCO3 (aq; sat.), dried over sodium sulfate and concentrated. The crude product was used in the next reaction without any further purification. Yield: 7.3 g, 37.8%.

Workup

  1. temperatureheated
  2. customhad formed
  3. temperatureThe temperature was raised to 120° C.
  4. temperatureheated
  5. temperatureat reflux for 24 h
  6. temperaturethe reaction mixture was then cooled on an ice bath
  7. dissolutionhad dissolved
  8. customThe aqueous layer was separated
  9. washwashed with NaHCO3 (aq; sat.)
  10. dry with materialdried over sodium sulfate
  11. concentrationconcentrated
  12. customThe crude product was used in the next reaction without any further purification

Sources & evidence

ORD record
ord-d83b9754a58b4fee80bfe9553254072d
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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