Acetonitrile → 3-(3-Methoxyphenyl)-3-oxopropanenitrile

HRID 1695216

Reaction equation

HRID 1695216 reaction equation
C(O[C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)C.[H-].[Na+].[CH3:16][C:17]#[N:18]>C1(C)C=CC=CC=1>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:4](=[O:13])[CH2:16][C:17]#[N:18])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 66299Benzoic acid, 3-methoxy-, ethyl ester

Product 1

HCID 5847163-(3-Methoxyphenyl)-3-oxopropanenitrileYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of commercially available 3-methoxy-benzoic acid ethyl ester (3.2 g, 18 mmol) in dry toluene (25 mL), under N2, NaH (50-60% dispersion in mineral oil, 1.44 g, 36 mmol) was carefully added. The mixture was heated at 90° C. and anhydrous CH3CN was added dropwise (4.45 mL, 85.2 mmol). The reaction was heated for 18 hours and the product precipitated from the reaction mixture as Na salt. The reaction was allowed to cool down to room temperature and the solid formed was filtered and washed with ether, then it was redissolved in water and the solution acidified with 2N HCl solution to pH 3 when precipitation of title compound was observed. Filtration of the solid from the aqueous solution afforded 1.57 g of title product (50% yield).

Workup

  1. temperatureThe reaction was heated for 18 hours
  2. customthe product precipitated from the reaction mixture as Na salt
  3. temperatureto cool down to room temperature
  4. customthe solid formed
  5. filtrationwas filtered
  6. washwashed with ether
  7. dissolutionit was redissolved in water
  8. customthe solution acidified with 2N HCl solution to pH 3 when precipitation of title compound
  9. filtrationFiltration of the solid from the aqueous solution

Sources & evidence

ORD record
ord-79b9a39cafb1499c8389952c3d4672e3
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Linked notes

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