Acetic Acid → Dodecanenitrile

HRID 850379

Reaktionsgleichung

Reaktionsgleichung von HRID 850379
[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]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 7189CinnamoylbenzeneHCID 9032Potassium Cyanide

Produkt 1

HCID 17092Dodecanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8076Glycol monoethyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-09c379ede3af4a9fb74195064cc2b22e
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06017916

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