Methanesulfonic Acid → Methyl Ricinoleate

HRID 534281

Reaktionsgleichung

Reaktionsgleichung von HRID 534281
[C:1](PCC1C(CPC(C)(C)C)=CC=CC=1)(C)(C)C.CS(O)(=O)=O.[C:24]([O-:44])(=[O:43])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][C@@H:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[OH:36]>CO.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:24]([O:44][CH3:1])(=[O:43])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]/[CH:32]=[CH:33]\[CH2:34][C@@H:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[OH:36]

Komponenten

6

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

In a second experiment, Pd(OAc)2 (6.5 mg, 0.029 mmol) and α,α′-di-tert-butylphosphino-o-xylene (59 mg, 0.15 mmol) were dissolved in 30 mL of dry methanol. Subsequently, methanesulfonic acid (20 μL, 0.3 mmol) and ricinoleate (290 mmol). The reaction was allowed to proceed at reflux (i.e. at a temperature of around 65° C.) for 24 h (conv. 80%), and then an identical amount of freshly prepared catalyst was added to the reaction mixture. After another 24 h of reflux, the reaction had reached completion and the mixture was allowed to cool down to room temperature and the crystals were filtered off and washed with methanol. The reaction mixture was analyzed with GC and showed only methyl-12-oxo-stearate.

Aufarbeitung

  1. additionan identical amount of freshly prepared catalyst was added to the reaction mixture
  2. temperatureAfter another 24 h of reflux
  3. temperatureto cool down to room temperature
  4. filtrationthe crystals were filtered off
  5. washwashed with methanol

Quellen und Nachweise

ORD-Eintrag
ord-927b723baa494f7f89af89188547c8c3
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853434B2

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