Acetic Acid → (3,3-Dimethylbutan-2-ylidene)propanedinitrile

HRID 236225Notes

Reaction equation

HRID 236225 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[CH3:6][C:7]([CH3:12])([CH3:11])[C:8](=O)[CH3:9].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH3:6][C:7]([C:8]([CH3:9])=[C:2]([C:1]#[N:5])[C:3]#[N:4])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6416PinacoloneHCID 8010MalononitrileHCID 517165Ammonium Acetate

Product 1

HCID 534326(3,3-Dimethylbutan-2-ylidene)propanedinitrileYield 68.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 9.9 g of malononitrile, 26.25 g of 3,3-dimethyl-2-butanone, 1.45 g of ammonium acetate and 2.25 g of acetic acid dissolved in 100 ml of toluene was refluxed for about 16 hours with the aid of a Dean-Stark Trap. The reaction mixture was diluted with 120 ml of toluene and washed with 200 ml water. The organic phase was collected, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The resulting residue was distilled under vacuum to afford 15.2 g of 2-(1,1-dimethylethyl)-1,1-dicyano-1-propene as an oil. Yield 68%.

Workup

  1. temperaturewas refluxed for about 16 hours with the aid of a Dean-Stark Trap
  2. washwashed with 200 ml water
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. distillationThe resulting residue was distilled under vacuum

Sources & evidence

ORD record
ord-aa5428eb78a445e4ae7e7564a987dd8c
Source dataset
uspto-grants-1987_02
Patent number
US04643758

Reaction notes

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