Organic Syntheses Procedure

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Org. Synth. 1927, 7, 28

DOI: 10.15227/orgsyn.007.0028

3,5-DINITROANISOLE

[Anisole, 3,5-dinitro-]

Submitted by Frederic Reverdin

Checked by C. S. Marvel and Dorothy E. Bateman.

1. Procedure

A solution of sodium methoxide is prepared by dissolving 6.3 g. (0.27 atom) of sodium in 150 cc. of absolute methyl alcohol (Note 1) in a 1-l. flask provided with a reflux condenser. To this is added a solution of 50 g. (0.23 mole) of 1,3,5-trinitrobenzene (p. 541) in 550 cc. of absolute methyl alcohol. The mixture is boiled for about twenty minutes. The reflux condenser is then replaced by a still head and condenser, and about 300–350 cc. of alcohol is distilled. The residue in the flask is cooled to 20° and filtered.

The crude product is purified by recrystallization from hot ordinary methyl alcohol. On account of the low solubility of the dinitroanisole in hot methyl alcohol, the best results are obtained by boiling the crude product with a few grams of decolorizing carbon (Norite) in about 500 cc. of methyl alcohol, filtering the hot solution through a hot funnel, cooling the solution, filtering, and using the mother liquors for another extraction. After five extractions no more of the product is dissolved. The yield of pure product melting at 105° is 29–35 g. (63–77 per cent of the theoretical amount).

2. Notes

1. One liter of ordinary absolute methyl alcohol was treated with 5 g. of magnesium turnings and 0.1 g. of mercuric chloride, and then distilled as soon as the magnesium had dissolved.

Working with Hazardous Chemicals

The procedures in Organic Syntheses are intended for use only by persons with proper training in experimental organic chemistry. All hazardous materials should be handled using the standard procedures for work with chemicals described in references such as "Prudent Practices in the Laboratory" (The National Academies Press, Washington, D.C., 2011; the full text can be accessed free of charge at http://www.nap.edu/catalog.php?record_id=12654). All chemical waste should be disposed of in accordance with local regulations. For general guidelines for the management of chemical waste, see Chapter 8 of Prudent Practices.

In some articles in Organic Syntheses, chemical-specific hazards are highlighted in red "Caution Notes" within a procedure. It is important to recognize that the absence of a caution note does not imply that no significant hazards are associated with the chemicals involved in that procedure. Prior to performing a reaction, a thorough risk assessment should be carried out that includes a review of the potential hazards associated with each chemical and experimental operation on the scale that is planned for the procedure. Guidelines for carrying out a risk assessment and for analyzing the hazards associated with chemicals can be found in Chapter 4 of Prudent Practices.

The procedures described in Organic Syntheses are provided as published and are conducted at one's own risk. Organic Syntheses, Inc., its Editors, and its Board of Directors do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein.

The paragraphs above were added in September, 2014. The statements above do not supersede any specific hazard caution notes and safety instructions included in the procedure.

3. Discussion

3,5-Dinitroanisole can be prepared by the action of sodium methoxide on 1,3,5-trinitrobenzene.¹

References and Notes