Acetonitrile → 3-(4-Ethoxyphenyl)-3-oxopropanenitrile

HRID 654596Notes

Reaction equation

HRID 654596 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10]CC)=O)=[CH:6][CH:5]=1)[CH3:2].[O-]CC.[Na+].[C:19](#[N:21])[CH3:20]>C1(C)C=CC=CC=1.O>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([CH2:20][C:19]#[N:21])=[O:10])=[CH:13][CH:14]=1)[CH3:2]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 90232Benzoic acid, 4-ethoxy-, ethyl esterHCID 2723922Sodium ethoxide

Product 1

HCID 222416953-(4-Ethoxyphenyl)-3-oxopropanenitrileYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Ethyl 4-ethoxybenzoate (45.3 mL, 250 mmole) was added to a suspension of sodium ethoxide (17.0 g, 250 mmole) and acetonitrile (16 mL, 300 mmole) in dry toluene (100 mL) and the mixture was mechanically stirred at 106°-110° for 26 hours. The reaction was then cooled and diluted with water (400 mL). After most of the solid had dissolved, the solution was washed with ethyl ether (2×200 mL) and then acidified with concentrated HCl (approximately 20 mL) to pH of about 5. The copious off-white precipitate was collected by suction filtration and air dried. Crystallization from 95% ethanol (350 mL) provided 21.3 g. of the subtitled compound as white needles, sufficiently pure for further transformation (yield: 45%). 1H NMR (CDCl3, δ) 7.85 (d, 2H, J=8 Hz, o-phenyl), 6.95 (d, 2H, J=8 Hz, m-phenyl), 4.1 (q, 2H, J= 7 Hz, OCH2), 4.0 (s, 2H, CH2CN), 1.45 (t, 3H, CH3).

Workup

  1. temperatureThe reaction was then cooled
  2. dissolutionAfter most of the solid had dissolved
  3. washthe solution was washed with ethyl ether (2×200 mL)
  4. filtrationThe copious off-white precipitate was collected by suction filtration and air
  5. customdried
  6. customCrystallization from 95% ethanol (350 mL)
  7. customprovided 21.3 g

Sources & evidence

ORD record
ord-1a5901f5777343549ee7706194660655
Source dataset
uspto-grants-1992_07
Patent number
US05132424

Reaction notes

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