Organic Syntheses, CV 1, 390
Submitted by Kurt H. Meyer
Checked by J. B. Conant and W. C. Boyd.
1. Procedure
In a
1-l. beaker equipped with a
separatory funnel, a
mechanical stirrer, and a
thermometer,
20 g. (0.1 mole) of anthrone (p. 60) is dissolved in
300 cc. of glacial acetic acid. While the mixture is kept at 60° and stirred, a solution of
10.5 g. (7 cc., 0.16 mole) of fuming nitric acid (sp. gr. 1.5) in
50 cc. of glacial acetic acid is run in during one hour.
On cooling to about 10°,
15 g. of
nitroanthrone separates out in long yellowish-white needles. After the addition of 100 cc. of water to the mother liquor,
6 g. more, somewhat darker in color, crystallizes in three to four hours.
On recrystallization from about
300 cc. of a 1:1 benzene-petroleum ether (40–60°) mixture,
16.5 g. of
nitroanthrone melting at
140° (corr.) is obtained (
67 per cent of the theoretical amount) (Note
1).
2. Notes
3. Discussion
This preparation is referenced from:
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