A
500-ml., three-necked, round-bottomed flask is fitted with a
gas-inlet tube, a
rubber septum, a
reflux condenser connected to a
mineral oil bubbler, and a sealed
mechanical stirrer. The system is flamed with a
Bunsen burner as it is flushed with dry
nitrogen. The reaction vessel is cooled under
nitrogen in an
ice bath, and
7.25 g. (0.125 mole) of 2-propen-1-ol (Note
1),
70 ml. of pentane (Note
2), and
1.16 g. (0.0100 mole) of N,N,N',N'-tetramethyl-1,2-ethanediamine (Note
3) are added successively through the rubber septum with a syringe. While maintaining a positive
nitrogen pressure,
180 ml. of 1.5 M (0.270 mole) n-butyllithium in
pentane (Note
4) is added from a syringe over a 20-minute period (Note
5). The ice bath is removed, and the reaction mixture is stirred for an additional hour (Note
6). The ice bath is then restored, the gas-inlet tube replaced with a
pressure-equalizing dropping funnel, and 70 ml. of water is added, cautiously at first, and then more rapidly after the exothermic reaction ceases. The resulting mixture is transferred to a
separatory funnel, the aqueous layer is separated and discarded, and the
pentane layer is washed with a
10-ml. portion of 3 N hydrochloric acid, then two 10-ml. portions of water. The organic layer is dried over anhydrous
magnesium sulfate and filtered. The solvent is removed by distillation through a
20-cm. Vigreux column. Distillation of the residual oil through a short-path distillation apparatus yields
9.3–9.6 g. (
64–66%) (Note
7) of
2-methyl-1-hexanol, b.p.
166–167° (Note
8) and (Note
9).