A solution of
sodium amide in liquid ammonia is prepared according to a procedure previously described (Note
1) in a
3-l. three-necked round-bottomed flask equipped with a
cold-finger condenser (cooled with Dry Ice) attached through a
soda-lime tower to a gas-absorption trap,
2 a
mercury-sealed stirrer, and an
inlet tube. Anhydrous
liquid ammonia (1 l.) is introduced from a commercial cylinder through the inlet tube, and
1 g. of hydrated ferric nitrate is added, followed by
80.5 g. (3.5 g. atoms) of clean, freshly cut sodium (Note
1) and (Note
2). The inlet tube is replaced with a
250-ml. dropping funnel, and the mixture is stirred until all the
sodium is converted into
sodium amide, after which
120.5 g. (1 mole) of tetrahydrofurfuryl chloride3 (Note
3) is added over a period of 25 to 30 minutes. The mixture is stirred for an additional period of 1 hour, after which
177 g. (3.3 moles) of solid ammonium chloride is added in portions at a rate that permits control of the exothermic reaction. The flask is allowed to stand overnight in the hood while the
ammonia evaporates. The residue is extracted thoroughly with ten
250-ml. portions of ether, which are decanted through a
Büchner funnel (Note
4). The
ether is distilled, and the residue is fractionated at a reflux ratio of about 5 to 1, through a
column containing a 20-cm. section packed with glass helices yielding
63–71 g. (
75–85%) of
4-pentyn-1-ol, b.p.
70–71° /29 mm.,
nD25 1.4443 (Note
5).