Sodium Cyanide → 12-t-Butylazo-12-cyanostearic Acid

HRID 1579172

Reaktionsgleichung

Reaktionsgleichung von HRID 1579172
O=C(CCCCCC)CCCCCCCCCCC(O)=O.ClCl.[C:24]([N:28]=[N:29][C:30](Cl)([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([OH:43])=[O:42])([CH3:27])([CH3:26])[CH3:25].[C-:51]#[N:52].[Na+]>CCCCC.CO.O>[C:24]([N:28]=[N:29][C:30]([C:51]#[N:52])([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][C:41]([OH:43])=[O:42])([CH3:27])([CH3:26])[CH3:25]

Komponenten

8

Edukt 4

HCID 8929Sodium CyanideHCID 24526ChlorineHCID 9477012-Oxooctadecanoic acidHCID 2156759612-t-Butylazo-12-chlorostearic acid

Produkt 1

HCID 2031824112-t-Butylazo-12-cyanostearic AcidAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8003PentaneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a solution of 21.0 grams (0.0568 moles) of the t-butylhydrazone of 12-ketostearic acid in 50 ml of pentane, cooled to -20°C, was passed 2.02 grams (0.0285 moles) of chlorine over a 10 minute period. The reaction was stirred an additional 15 minutes at -20°C, the white solid that formed, filtered off, and the pentane filtrate, which should contain approximately 0.0285 moles of 12-t-butylazo-12-chlorostearic acid added to a solution of 1.5 grams (0.03 moles) of sodium cyanide in 20 mls of 75% aqueous methanol. The reaction was stirred for 1 hour at 20°C, poured into 100 ml of water, the pentane layer separated, washed with 5% HCl and then with water until neutral. The pentane solution was dried over anhydrous sodium sulfate, filtered and the pentane evaporated under reduced pressure to leave 8.5 grams (76% yield) of the desired acid.

Aufarbeitung

  1. customover a 10 minute
  2. customthe white solid that formed
  3. filtrationfiltered off
  4. stirringThe reaction was stirred for 1 hour at 20°C
  5. customthe pentane layer separated
  6. washwashed with 5% HCl
  7. dry with materialThe pentane solution was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customthe pentane evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1b08e019ef06433aa579283cb9f4be79
Quelldatensatz
uspto-grants-1976_01
Patentnummer
US03931143

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