Hydrochloric Acid → 4-Formyl-4-methylvaleronitrile

HRID 1174468Notes

Reaction equation

HRID 1174468 reaction equation
[CH:1](=[O:5])[CH:2]([CH3:4])[CH3:3].[C:6](#[N:9])[CH:7]=[CH2:8].Cl>CO>[CH3:3][C:2]([CH3:4])([CH:1]=[O:5])[CH2:8][CH2:7][C:6]#[N:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 7855Acrylonitrile

Product 1

HCID 802314-Formyl-4-methylvaleronitrileYield 50.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Isobutyraldehyde (1 g, 13.9 mmol) and acrylonitrile (0.81 g, 15 mmol) were mixed thoroughly and cooled with an ice-bath. Triton B (40% in MeOH, 0.58 g, 1.4 mmol) was added. The mixture was stirred at room temperature overnight. It was then neutralized with 0.1 M HCl (14 cm3) and extracted with CH2Cl2 (100 cm3). The extracts were concentrated under reduced pressure and the residue was Kugelrohr-distilled to give the product 4,4dimethyl-5-oxopentanenitrile (0.8 g, 50.7%) as an oil, bp 125-130° C./20 Torr.

Workup

  1. temperaturecooled with an ice-bath
  2. extractionextracted with CH2Cl2 (100 cm3)
  3. concentrationThe extracts were concentrated under reduced pressure
  4. distillationthe residue was Kugelrohr-distilled

Sources & evidence

ORD record
ord-2912a3f19af140ff9af407582f365367
Source dataset
uspto-grants-2010_11
Patent number
US07838483B2

Reaction notes

Loading…