Hydrochloric Acid → 2-(4-Ethenylphenyl)ethane-1,1,2-tricarbonitrile

HRID 1452451Notes

Reaction equation

HRID 1452451 reaction equation
[C:1]([C:3]([C:13]#[N:14])=[CH:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)#[N:2].C(O)C.[C-:18]#[N:19].[K+].Cl>O>[C:18]([CH:4]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH2:10])=[CH:7][CH:6]=1)[CH:3]([C:1]#[N:2])[C:13]#[N:14])#[N:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 9032Potassium CyanideHCID 21977170[(4-Ethenylphenyl)methylidene]propanedinitrile

Product 1

HCID 219771712-(4-Ethenylphenyl)ethane-1,1,2-tricarbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2.00 g 4-(2,2′-dicyanoethenyl)styrene (11 mmol) and 30 mL ethanol was added a solution of 1.45 g potassium cyanide (22 mmol) in 3 mL water. The mixture was stirred at room temperature for 17 hours. 1.8 mL concentrated HCl (22 mmol) was then added and the mixture was concentrated under vacuum. Ten milliliters (10 mL) water was added to the residue, and the mixture was extracted with ethyl acetate. The combined organic layers were concentrated under vacuum, and the product was purified by column chromatography on silica gel using 20% ethyl acetate in hexane. The product recovered from the separation was mixed with 1.5 mL methylene chloride and 10 mL hexane, then filtered. A white solid was obtained (1.009 g, 44%).

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. additionTen milliliters (10 mL) water was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. concentrationThe combined organic layers were concentrated under vacuum
  5. customthe product was purified by column chromatography on silica gel using 20% ethyl acetate in hexane
  6. customThe product recovered from the separation
  7. additionwas mixed with 1.5 mL methylene chloride and 10 mL hexane
  8. filtrationfiltered
  9. customA white solid was obtained (1.009 g, 44%)

Sources & evidence

ORD record
ord-e5150dd7463541798a91bc34ede41cd9
Source dataset
uspto-grants-2009_01
Patent number
US07473652B2

Reaction notes

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