Acetic Acid → Ethyl 2,6-dicyano-3-methylhex-2-enoate

HRID 1248747Notes

Reaction equation

HRID 1248747 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]([CH3:8])=O)#[N:2].[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12](=[O:13])[C:11]([C:9]#[N:10])=[C:6]([CH3:8])[CH2:5][CH2:4][CH2:3][C:1]#[N:2])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 82611Hexanenitrile, 5-oxo-HCID 517165Ammonium Acetate

Product 1

HCID 54500111Ethyl 2,6-dicyano-3-methylhex-2-enoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 3-cyanopropyl ketone (55.5 g, 0.5 mole), ethyl cyanoacetate (56.5 g, 0.5 mole), acetic acid (6.0 g, 0.1 mole), ammonium acetate (3.85 g, 0.05 mole) and toluene (50 ml) was refluxed while azeotropically removing the water of reaction formed. After 10 hours the solution was vacuum distilled and a fraction (b.p. 145° C.-153° C., 0.5 torr) was collected. Total yield was 77.0 g or 74.7 percent. Analysis by infrared spectroscopy confirmed the product's identity as:

Workup

  1. temperaturewas refluxed
  2. customwhile azeotropically removing
  3. customthe water of reaction
  4. customformed
  5. distillationvacuum distilled
  6. customa fraction (b.p. 145° C.-153° C., 0.5 torr) was collected

Sources & evidence

ORD record
ord-51ec1de1199247a28bbbdefc3a56315e
Source dataset
uspto-grants-1985_06
Patent number
US04525577

Reaction notes

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