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29th August 2013 @ 10:23

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Reaction information

*#Reaction file
reactionscheme_26 .cdx
*Reaction file type CDX
*Procedure Repeating the procedure described by Loupy, in a sealed Schlenk tube hydroquinone (0.55 g, 4.99 mmol), Tetrabutylammonium bromide, TBAB (63 mg, 9% w/w KOH) and KOH powder (0.7 g, 12.47 mmol, 2.50 eq.) were stirred for 10 minutes before adding octylbromide (2.16 mL, 2.42 g, 12.53 mmol, 2.51 eq.) and heating to 80 ºC for 17 h. The reaction mixture was then dissolved in Et2O and washed with water, the organic phase was dried over anhydrous MgSO4and the solvent evaporated to afford the crude title compound (1.87 g). The pure product (1.03 g, 3.08 mmol) was obtained by column chromatography on silica gel, using as eluent (5/1) hexane/DCM (Rf0.15); this was then recrystallized from EtOH as white thin flakes (0.77 mg, 2.30 mmol, yield 46%).
*Yield (%) 46 %
*Type of Yield Isolated pure product
Reference(s)

PhD Thesis - 16Sep2010_final p14.pdf
PhD Thesis - 16Sep2010_final p120.pdf

Loupy, A.; Sansoulet, J.; Diez-Barra, E.; Carrillo, J. R. Synth. Comm1991, 21, 1465-1471.

Further information Compound 26: 1,4-bis(octyloxy)benzene

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 Reaction 27: Halogenation of 1,4-bis(octyloxy)benzene with Iodine: 1,4-diiodo-2,5-bis(octyloxy)benzene
For step in multistep reaction - link to following reaction step  
Attached Files
PhD Thesis - 16Sep2010_final p120.pdf
reactionscheme_26 .cdx