Methanesulfonic Acid → Methyl Ricinoleate

HRID 534281Notes

Reaction equation

HRID 534281 reaction equation
[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]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 16690250alpha,alpha'-Di-tert-butylphosphino-o-xyleneHCID 25630959Ricinoleate

Product 1

HCID 5354133Methyl Ricinoleate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-927b723baa494f7f89af89188547c8c3
Source dataset
uspto-grants-2014_10
Patent number
US08853434B2

Reaction notes

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