Fifty-one grams (0.30 mole) of sebacoin (Note
1),
25 ml. of methanol,
120 g. of cupric acetate monohydrate (0.60 mole), and
300 ml. of 50% aqueous acetic acid are mixed in a
1-l. flask equipped with an
efficient mechanical stirrer and a
reflux condenser. The mixture is heated over a free flame until refluxing occurs. The color of the mixture changes from blue to red at approximately 75°. Refluxing is continued for 1 minute. The mixture is then allowed to cool, with stirring, to about 40° (Note
2). The mixture is filtered through filter aid ("Celite") on a
sintered glass funnel to remove
cuprous oxide, and the filtrate is transferred to a
2-l. separatory funnel (Note
3). Saturated aqueous
sodium chloride solution. (310 ml.) is added to the filtrate, which is then extracted with three
150-ml. portions of ether. The combined
ether extracts are washed with three 250-ml. portions of saturated salt solution, four
250-ml. portions of 5% sodium bicarbonate solution (foaming!), and once again with 250 ml. of saturated salt solution. The
ether solution is then dried over
20 g. of anhydrous sodium or magnesium sulfate. The
ether is removed by distillation at atmospheric pressure, and the residue is transferred to a
100-ml. flask and distilled under vacuum. The yield of
sebacil is
44.4–45.1 g. (
88–89%), b.p.
104–106°/10 mm. (Note
4).