Acetic Acid → Dodecanenitrile

HRID 850379Notes

Reaction equation

HRID 850379 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)C=CC=[CH:3][CH:2]=1.C(O)(=O)C.[C-]#[N:22].[K+]>C(OCCO)C.O>[CH3:3][CH2:2][CH2:1][CH2:7][CH2:8][CH2:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:22]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7189CinnamoylbenzeneHCID 9032Potassium Cyanide

Product 1

HCID 17092Dodecanenitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8076Glycol monoethyl etherSolvent

Conditions

Temperature
105 °C

Procedure

To the chalcone, 187, (17.95 g, 54.7) mmol) in 2-ethoxyethanol (150 mL) at 55° C. was added acetic acid (4 mL) followed by slow addition of potassium cyanide (5.3 g, 81 mmol) in water. The solution was stirred at 105° C. for 0.25 hour. The solution was cooled and treated with water (25 mL). The mixture was filtered to collect the solid. The solid was washed repeatedly with 70% ethanol (50 mL), air dried, and then dried in vacuo to give the nitrile 12.7 g (68%) as a yellow solid. The nitrile was identified by 1H NMR, IR, MS, and microanalysis.

Workup

  1. temperatureThe solution was cooled
  2. filtrationThe mixture was filtered
  3. customto collect the solid
  4. washThe solid was washed repeatedly with 70% ethanol (50 mL), air
  5. customdried
  6. customdried in vacuo

Sources & evidence

ORD record
ord-09c379ede3af4a9fb74195064cc2b22e
Source dataset
uspto-grants-2000_01
Patent number
US06017916

Reaction notes

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