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23rd August 2013 @ 08:39

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Reaction information

*#Reaction file
reactionscheme_5 .cdx
*Reaction file type CDX
*Procedure Following the procedure described by Maillard, in a 250 mL Schlenk flask, fitted with a reflux condenser, dodecylmagnesium bromide (formed from Mg 2.91 g and 1-dodecylbromide 29.9 g, 120 mmol, 1.00 eq.) was diluted in Et2O (120 mL) to obtain a 1 M solution. This was added dropwise by cannula to a 250 mL Schlenk flask, fitted with a reflux condenser, containing 1,4-dichlorobenzene (7.35 g, 50.0 mmol; recrystallized from EtOH) and NiCl2-dppp (68 mg, 25 mol%), previously evacuated and refilled with Ar, and cooled in a ice bath under positive pressure of Ar. The ice bath was removed and when the mixture was at r.t. the reaction was initiated by heating the flask for few seconds with a heat-gun. After 4 h the mixture was heated to reflux (50 ºC) and stirred overnight. The unreacted alkylmagnesium bromide was then quenched with a solution of HCl 2N (aq. 70 mL), while cooling the flask in an ice bath. The two layers were separated and the aqueous phase was extracted three times with Et2O; the combined organic phases were washed with water, NaHCO3 (sat.), again water and dried over anhydrous MgSO4. Evaporation of the solvent afforded the crude product as white solid (23.79 g). The by-products of the reaction, mostly dodecane, were removed by distillation in a Kugelrohr apparatus, at 200 ºC, over 3.5 h. The resulting pure product (18.09 g) was recrystallized overnight from MeOH as white microcrystalline powder (17.81 g, 42.9 mmol, yield 86%)
*Yield (%) 86 %
*Type of Yield Isolated pure product
Reference(s)

PhD Thesis - 16Sep2010_final p12.pdf
PhD Thesis - 16Sep2010_final p107.pdf

Maillard, M.; Motte, L.; Ngo, A. T.; Pileni, M. P. JPhysChemB 2000, 104, 11871-11877.

Further information Compound 5: 1,4-Didodecylbenzene

For multistep reactions (or their steps):

Overall reaction? False
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step Reaction 6: Halogenation of 1,4-didodecylbenzene with Iodine: 1,4-didodecyl-2,5-diiodobenzene
Attached Files
PhD Thesis - 16Sep2010_final p12.pdf
reactionscheme_5 .cdx
PhD Thesis - 16Sep2010_final p107.pdf