Acetonitrile → Pentanenitrile, 4,4-dimethyl-3-oxo-

HRID 986827Notes

Reaction equation

HRID 986827 reaction equation
[H-].[Na+].[C:3]([O:9]C)(=O)[C:4]([CH3:7])([CH3:6])[CH3:5].[C:11](#[N:13])[CH3:12].[H][H]>C1(C)C=CC=CC=1.O>[C:3]([CH2:12][C:11]#[N:13])(=[O:9])[C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 69027Methyl pivalateHCID 178418361HCID 178418361, compound

Product 1

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

55 grams of sodium hydride (as an 80 weight % suspension in white oil) were suspended in 500 ml of dry toluene, 106 grams (0.914 mole) of methyl pivalate added and the mixture heated to 85° C. Then under vigorous stirring there were dropped in 77 grams (1.87 moles) of acetonitrile within 4 hours. Stirring was continued subsequently at 85° C. until the end of the development of hydrogen. The thickly liquid reaction mass was cooled to room temperature, treated with 700 ml of water, stirred vigorously for 30 minutes and the two phases separated in a separatory funnel. The aqueous phase was acidified with 31 weight % of hydrochloric acid at a pH 1-2 and 0° C. The precipitated pivaloylacetonitrile was filtered off with suction, washed until neutral with ice water and dried to constant weight at 25 Torr and 40° C. There were obtained 106 grams (93% of theory) of analytically pure pivaloylacetonitrile having a melting point of 65°-68° C.

Workup

  1. stirringStirring
  2. customThe thickly liquid reaction mass
  3. temperaturewas cooled to room temperature
  4. stirringstirred vigorously for 30 minutes
  5. customthe two phases separated in a separatory funnel
  6. customwas acidified with 31 weight % of hydrochloric acid at a pH 1-2 and 0° C
  7. filtrationThe precipitated pivaloylacetonitrile was filtered off with suction
  8. washwashed until neutral with ice water
  9. customdried to constant weight at 25 Torr and 40° C

Sources & evidence

ORD record
ord-4953832d6a0d4af1bd8a35bca85f9f32
Source dataset
uspto-grants-1987_12
Patent number
US04716237

Reaction notes

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