Reaction equation
[C:1]([O:21][CH3:22])(=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@@H:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[OH:13].COC(=O)C(C)CCCCCC/C=C\C[C@@H](CCCCCC)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:22][O:21][C:1](=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12](=[O:13])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]Participants
5
Conditions
- Temperature
- 120 °C
Procedure
1.52 g Aliquat 100 (tetrabutyl ammonium bromide, TBAB) and 8.3 mg Pd(OAc)2 were placed in a 5 mL vial with crimp cap. This mixture was heated to 120° C. under vacuum for 2.5 hours. The vial was put under N2-atmosphere and 312 mg (1 mmol) methyl ricinoleate was added. This mixture was heated to 120° C. for 94 hours. The product was extracted from the TBAB with heptane. After concentration 172 mg was obtained. The reaction products were analyzed by GC (FIG. 11): 8 area % methyl ricinoleic acid methyl ester, 15 area % at 2.54′, 21 area % at 11.8′, 20 area % at 12.77′ and 33 area % at 13.69′. No 12-oxostearate methyl ester was formed.
Workup
- temperatureThis mixture was heated to 120° C. for 94 hours
- extractionThe product was extracted from the TBAB with heptane
- customAfter concentration 172 mg was obtained
Sources & evidence
- ORD record
- ord-0d3c693fcb484dae9ad4cdd7a8da6024
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853434B2
Linked notes
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