Acetonitrile → 4-Methyl-3-carbonyl valeronitrile

HRID 1772180Notes

Reaction equation

HRID 1772180 reaction equation
[C:1](OC)(=O)[CH:2]([CH3:4])C.[O-:8][CH2:9][CH3:10].[Na+].[C:12](#[N:14])[CH3:13]>CO>[CH3:1][CH:2]([CH3:4])[C:10](=[C:9]=[O:8])[CH2:13][C:12]#[N:14]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 11039Methyl isobutyrateHCID 2723922Sodium ethoxide

Product 1

HCID 866857984-Methyl-3-carbonyl valeronitrile

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 1 L of round bottom flask were added methyl isobutyrate (100 g, 0.98 mol), sodium ethoxide (66.63 g, 0.98 mol), acetonitrile (53.9 g, 0.98 mol) and 300 ml of methanol at room temperature. The resultant mixture was slowly warmed and refluxed. The reaction was kept for 6 hr. The reaction was stopped and cooled to room temperature. The solvent was rotary-evaporated. The product was distilled under reduced pressure (12 mmHg) to collect at 102-104° C. 56.2 g of the pure title compound.

Workup

  1. temperaturerefluxed
  2. customThe solvent was rotary-evaporated
  3. distillationThe product was distilled under reduced pressure (12 mmHg)
  4. customto collect at 102-104° C

Sources & evidence

ORD record
ord-e8b5ee671ec84da7bdcf9070e0f4e98a
Source dataset
uspto-grants-2016_02
Patent number
US09249172B2

Reaction notes

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