Organic Syntheses, Coll. Vol. 1, p.219 (1941); Vol. 7, p.28 (1927).
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.
per cent of the theoretical amount).
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