9-Octadecene, 1-bromo-, (9Z)- → (Z)-9-Tricosene

HRID 1604860Notes

Reaction equation

HRID 1604860 reaction equation
[CH2:1](Br)[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].[CH2:20]([Mg]Br)[CH2:21][CH2:22][CH2:23][CH3:24]>O1CCCC1>[CH3:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 58403839-Octadecene, 1-bromo-, (9Z)-HCID 178445865HCID 178445865, compound

Product 1

HCID 5365075(Z)-9-Tricosene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In contrast, the reaction of one equivalent of oleyl bromide with 1.2 equivalents of amyl-magnesium bromide and 5% m/m lithium dichlorocuprate in tetrahydrofuran at -25° to -15° and using a procedure identical to that of Example 7 gave about 80% conversion to crude Z-9-tricosene. The remainder of the product is Z-1,9-octadecadiene.

Sources & evidence

ORD record
ord-fdb4dedae5b64f8eb75da36de5cd9bc3
Source dataset
uspto-grants-1976_04
Patent number
US03948803

Reaction notes

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