Toluene → CID 521661

HRID 1430391Notes

Reaction equation

HRID 1430391 reaction equation
[CH2:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:17]1(C)C=CC=C[CH:18]=1>CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=C3C4C(=CC=CC=4)C(C4C=CC=CC=4)=C3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.CCCCC>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 1140TolueneHCID 8058HexaneHCID 133811-Decene

Product 1

HCID 521661CID 521661

Reagents, catalysts & solvents 2

HCID 72376333Tricyclohexylphosphine[3-phenyl-1H-inden-1-ylidene][1,3-bis(2,4,6-triMethylphenyl)-4,5-dihydroiMidazol-2-ylidene]rutheniuM(II)CatalystHCID 8003PentaneSolvent

Procedure

1-Decene (5.00 mL, 26.4 mmol) and hexane (10 mL) were heated to reflux on a heating block kept at 75° C. Then a toluene (2 mL) solution of Neolyst M2 (0.0836 g, 0.0880 mmol) was added. Gas evolution was observed. After 18 hours the mixture was cooled to ambient temperature, and pentane (18 mL) was added. The mixture was passed through a plug of neutral alumina. The volatiles were then removed under reduced pressure to afford a colorless oil of 9-octadecene. Yield: 3.12 g. Proton NMR data shows greater than 95% conversion to homocoupled product.

Workup

  1. temperatureto reflux on a heating block
  2. customkept at 75° C
  3. customThe volatiles were then removed under reduced pressure

Sources & evidence

ORD record
ord-83c1aec47cdc421db39757b72dc95d3b
Source dataset
uspto-grants-2015_01
Patent number
US08940839B2

Reaction notes

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