Chlorobenzene → Undecane

Participants

Reaction Steps

THF (0.10 mL) was added to rinse the internal wall of the reaction vessel. After 10 hours, a THF solution of mesitylmagnesium bromide (1.02 mL, 1.18 M, 1.2 mmol) was added to the mixture at 0° C., and the solvent was removed under reduced pressure. The obtained viscous liquid was dissolved in toluene (1.0 ml), and chlorobenzene (112.6 mg, 1.0 mmol) was added at 0° C. The reaction was performed at 120° C. for 24 hours. After cooled to the ambient temperature, 2.0 mL of saturated sodium potassium tartrate aqueous solution was added to the reaction mixture. The water layer was extracted five times using Et2O. The total organic extract was filtrated by Florisil pad (100-200 mesh, Nacalai Tesque, Inc.). As the internal standard, gas chromatographic analysis was performed using undecane (42.2 μL, 0.2 mmol) (yield=93%). After removing the solvent under reduced pressure, the crude product was purified by GPC, thereby obtaining the above compound, which was a colorless liquid (0.174 g, yield=89%, purity=>99% (GC analysis)).

Provenance & Evidence