5-Nitro furfural diacetate prepn. - by nitration of furfural in acetic anhydride

5-Nitrofurfural diacetate (I) is prepd. by (a) adding furfural (II) (or a soln. of furfural diacetate (III) in acetic anhydride) and a mixt. of HNO3 and H2SO4 simultaneously to stirred acetic anhydride at -10 to +10 degrees C at rates such that a molar ratio of (II) or (III) to HNO3 and H2SO4 of 1:1...

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Main Author S. A. GILLER, K. K. VENTER, M. A. TRUSHULE, G. E. BERGGRIN, R. A. BRINKMANIS, U. Y. MIXTAIS ET P. A. STANKEVICH
Format Patent
LanguageEnglish
French
Published 11.03.1977
Subjects
CHEMISTRY
HETEROCYCLIC COMPOUNDS
METALLURGY
ORGANIC CHEMISTRY
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Summary:5-Nitrofurfural diacetate (I) is prepd. by (a) adding furfural (II) (or a soln. of furfural diacetate (III) in acetic anhydride) and a mixt. of HNO3 and H2SO4 simultaneously to stirred acetic anhydride at -10 to +10 degrees C at rates such that a molar ratio of (II) or (III) to HNO3 and H2SO4 of 1:1.1-2:0.036-0.041 is maintained and the teamp. remains between -10 and +10 degrees C; (b) treating the reaction mixt. at 0-15 degrees C with 1.1-1.8 pts. wt. H2O per pt. wt. of Ac2O initially the present; (c) adjusting the pH to 3.5-5 with alkali at 0-25 degrees C; (d) keeping the mixt. at 45-55 degrees C; and (e) isolating the prod. (I) is used as a starting material for the prepn. of chemotherapeutic agents for use in medicine and agriculture. The process avoids the formation of explosive mixts. of acetyl nitrate and Ac2O, and gives high yields (e.g. 78-85%) of high-purity (I).
Bibliography:Application Number: FR19750025118