Isopropanol → 1-Decene

HRID 1477089Notes

Reaction equation

HRID 1477089 reaction equation
[C:1]([O:20][CH3:21])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12]CCCCCC.C=CCC.C(O)(C)C>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.OCP(CO)CO>[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:1][CH2:2][CH:3]=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:21][O:20][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].[CH3:21][O:20][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH3:12]

Participants

9

Reactant 3

HCID 3776IsopropanolHCID 78441-Butene2×HCID 5364509Methyl Oleate

Product 4

HCID 133811-DeceneHCID 1372853-DodecenHCID 534675Methyl 9-dodecenoateHCID 1778877Methyl 9-decenoate

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 76001Tris(Hydroxymethyl)PhosphineSolvent

Conditions

Temperature
60 °C

Procedure

Methyl oleate (20 mol) and a second-generation Grubbs' catalyst (e.g., C827, 25 ppm) are added to a Parr Reactor and degassed with argon for 1 hr. 1-Butene is added while heating to 60° C. while keeping the pressure of the reaction between about 25 to about 60 psi. The 1-butene is added using a one-way check valve to prevent backflow into the 1-butene cylinder. After 4 hrs, the pressure is released and vented into the fume hood. After allowing the reactor to cool to room temperature, a 50 ml 1M tris-hydroxymethylphosphine (THMP) solution in isopropanol (IPA) (50 mol equiv.) is added, and the reactor is degassed with argon and heated to 60° C. for 18 hrs. The reactor is then again allowed to cool to room temperature. The crude reaction product is then washed with water and brine. The washed reaction product is them dried over sodium sulfate, filtered, and distilled to provide 1-decene, 3-dodecene, 9-decenoic acid methyl ester, and 9-dodecenoic acid methyl ester.

Workup

  1. customdegassed with argon for 1 hr
  2. addition1-Butene is added
  3. customthe pressure of the reaction between about 25 to about 60 psi
  4. temperatureto cool to room temperature
  5. customthe reactor is degassed with argon
  6. temperatureheated to 60° C. for 18 hrs
  7. temperatureto cool to room temperature
  8. customThe crude reaction product
  9. washis then washed with water and brine
  10. customThe washed reaction product
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. distillationdistilled

Sources & evidence

ORD record
ord-f0deb757930a4cb2b857d32495b779c1
Source dataset
uspto-grants-2016_08
Patent number
US09403752B2

Reaction notes

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