Water → Benzoylacetonitrile

HRID 654592Notes

Reaction equation

HRID 654592 reaction equation
[O-]CC.[Na+].[C:5]([O:13]CC)(=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:16](#[N:18])[CH3:17].O>C1(C)C=CC=CC=1>[C:5]([CH2:17][C:16]#[N:18])(=[O:13])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 7165Ethyl benzoateHCID 2723922Sodium ethoxide

Product 1

HCID 64799Benzoylacetonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of sodium ethoxide (34.0 g. 0.500 mole) in dry toluene (200 mL were added ethyl benzoate (71.4 mL, 0.500 mole) and dry acetonitrile (32 mL, 0.60 mole). The mixture was mechanically stirred under nitrogen at 105°-110° C. for 29 hours, during which time it became quite viscous. After cooling to room temperature, water (300 mL) was added and the mixture was washed with ethyl ether (2×100 mL). The aqueous layer was then acidified to pH 5-6 with con. aq. HCl (required 30-35 mL) and the resulting crystalline precipitate was collected by suction filtration, washed twice with water, and air-dried. This subtitled material (49.23 g, 68%, m.p. 72°-73°) was sufficiently pure to be used in further transformations (lit., m.p. 80°-81°, Long, R. S., J. Am. Chem. Soc., (1947), 69, p. 990. 1NMR (CDCl3, δ) 7.95 (dd, 2H, J=7, 2 Hz, o-aryl), 7.6 (m, 3H, aryl), 4.1 (s, 2H, CH2). This benzoyl acetonitrile intermediate is also now commercially available but we prepared ours as above.

Workup

  1. washthe mixture was washed with ethyl ether (2×100 mL)
  2. filtrationaq. HCl (required 30-35 mL) and the resulting crystalline precipitate was collected by suction filtration
  3. washwashed twice with water
  4. customair-dried
  5. customwe prepared ours as above

Sources & evidence

ORD record
ord-c486430ce1b94b25a765b480b6a22509
Source dataset
uspto-grants-1992_07
Patent number
US05132424

Reaction notes

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