Acetonitrile → 2-Methoxybenzoylacetonitrile

HRID 2166477Notes

Reaction equation

HRID 2166477 reaction equation
[H-].[Na+].CO[C:5](=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13].[C:15](#[N:17])[CH3:16]>C1(C)C=CC=CC=1>[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]([CH2:16][C:15]#[N:17])=[O:14]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 61151Methyl 2-Methoxybenzoate

Product 1

HCID 49627502-Methoxybenzoylacetonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

Into an agitation apparatus with agitator, dropping funnel, gas inlet tube and reflux cooler, under agitation and introduction of nitrogen, 28.8 g (0.6 mol) sodium hydride (as a 50 wt-% suspension in white oil) suspended in 200 ml absolute toluene and 49.9 g (0.3 mol) 2-methoxybenzoic acid methyl ester were introduced. The mixture was heated to 85° C. Within 2 hr, 24.6 g (0.5 mol) absolute acetonitrile was dropped into the heated mixture. Then the reaction mixture was further agitated for 15 hr at 90° C. The mixture was then cooled to 0° C., 300 ml ice water were added carefully under vigorous agitation, and then agitation was continued for 1 hr at 0° C. Then the aqueous phase was removed and extracted with 100 ml toluene. After cooling to 0° C. the aqueous phase was acidified with dilute hydrochloric acid to pH 1. The precipitated product was washed with ice water and dried. The crude product (44 g) was recrystallized from isopropanol; 37.9 g (72% of the theoretical) 2-methoxybenzoylacetonitrile with m.p. 85°-88° were obtained.

Workup

  1. temperaturereflux cooler
  2. temperatureThe mixture was then cooled to 0° C.
  3. waitagitation was continued for 1 hr at 0° C
  4. customThen the aqueous phase was removed
  5. extractionextracted with 100 ml toluene
  6. temperatureAfter cooling to 0° C. the aqueous phase
  7. washThe precipitated product was washed with ice water
  8. customdried
  9. customThe crude product (44 g) was recrystallized from isopropanol

Sources & evidence

ORD record
ord-7ed28dab671345f29bb1bed83a81a330
Source dataset
uspto-grants-1990_07
Patent number
US04945177

Reaction notes

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