Methanesulfonic Acid → Methyl Ricinoleate

HRID 534281

반응식

HRID 534281 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 5354133Methyl Ricinoleate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-927b723baa494f7f89af89188547c8c3
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853434B2

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