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

HRID 1604859Notes

Reaction equation

HRID 1604859 reaction equation
[CH2:1]([Mg]Br)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:8](Br)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>O1CCCC1>[CH3:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 2

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

Product 1

HCID 5365075(Z)-9-TricoseneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1.15 moles of amylmagnesium bromide in 335 ml. anhydrous tetrahydrofuran at -8° is added 0.028 moles of lithium chlorocyanocuprate in tetrahydrofuran, prepared in Example 1 above. Dropwise addition of 1.00 moles of Z-9-octadecenyl bromide is carried out with cooling to maintain the temperature at from about -6° to +5°. The reaction mixture is maintained at -5° to +5° for 1 hour. Magnesium bromide is precipitated by the addition of hexane and a minor amount of water. The slurry of granular solid is filtered and washed with hexane. Evaporation of solvent from the filtrate gives a clear amber oil of Z-9-tricosene in 99% yield.

Workup

  1. customprepared in Example 1 above
  2. temperaturewith cooling
  3. temperatureto maintain the temperature at from about -6° to +5°
  4. temperatureThe reaction mixture is maintained at -5° to +5° for 1 hour
  5. customMagnesium bromide is precipitated by the addition of hexane
  6. filtrationThe slurry of granular solid is filtered
  7. washwashed with hexane
  8. customEvaporation of solvent from the filtrate

Sources & evidence

ORD record
ord-488faadc17c54209b6aa7220e80d1eed
Source dataset
uspto-grants-1976_04
Patent number
US03948803

Reaction notes

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