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Org. Synth. 1928, 8, 78
DOI: 10.15227/orgsyn.008.0078
NITROANTHRONE
[Anthrone, 10-nitro-]
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
1. By dissolving in hot alkali (about 300 cc. of water and 30 g. of sodium hydroxide per gram of nitroanthrone) and precipitating with acid below 10°, the red nitroanthranol may be obtained, which on standing slowly changes back to the nitroanthrone.
3. Discussion
Nitroanthrone can be prepared by the nitration of anthracene in isobutyl alcohol,1 and by the nitration of anthrone.2
This preparation is referenced from:

References and Notes
  1. Perkin and Mackenzie, J. Chem. Soc. 61, 868 (1892); Meisenheimer and Connerade, Ann. 330, 177 (1904).
  2. Meyer and Sander, Ann. 396, 149 (1913).

Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)

benzene-petroleum ether

acetic acid (64-19-7)

sodium hydroxide (1310-73-2)

nitric acid (7697-37-2)

Anthrone (90-44-8)

anthracene (120-12-7)

Nitroanthrone

Anthrone, 10-nitro- (6313-44-6)

nitroanthranol

isobutyl alcohol (78-83-1)