Isopropanol → 1-Decene

HRID 1496812노트

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HRID 1496812 반응식
[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]

참가 물질

9

반응물 3

HCID 3776IsopropanolHCID 78441-Butene2회HCID 5364509Methyl Oleate

생성물 4

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

시약·촉매·용매 2

HCID 178479819HCID 178479819, 화합물촉매HCID 76001Tris(Hydroxymethyl)Phosphine용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-093afb76bdff466d9db32fbf8f6fd496
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199911B2

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