Isopropanol → 1-Decene

HRID 1496812Notes

Reaction equation

HRID 1496812 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-093afb76bdff466d9db32fbf8f6fd496
Source dataset
uspto-grants-2015_12
Patent number
US09199911B2

Reaction notes

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