Butyl Chloride → HCID 178448197, compound

Participants

Reaction Steps

To a reaction mixture derived by cooking magnesium metal powder (0.30 g atoms) and n-butyl chloride (0.25 moles) together in 175 ml refluxing heptane was added a solution of 2-ethylhexylsodium (310 ml of 0.65N conc.) in heptane,2 the temperature of reaction not exceeding 42° C. On filtration of the reaction mixture, a solution which was 0.64N in total alkalinity and 0.34M in Mg was obtained. The solution was concentrated to 0.64M (2.2 wt. % Mg) in Mg (Na=0.0025M). Some precipitation of solids occurred in the solution on standing overnight (Mg=0.55M). Sufficient triisobutylaluminum in hexane solution was added to give a final Al concentration corresponding to 3 mole % on the total Mg. All solids immediately dissolved and a very fluid solution resulted. The viscosity of this solution was found to be only 1.25 cps (40° ), a significantly lower value than that listed for a commercial n-butylethylmagnesium in heptane solution at the same magnesium concentration (about 15 cps). Again, the viscosity lowering effect of the 2-ethylhexyl group, as well as its solubilizing properties, was noted. (Di-n-butylmagnesium alone possesses only a very low order [<0.2M] of solubility in hydrocarbon solvents.)

Provenance & Evidence