Process for selectively producing isosorbide-5-nitrate

Details Process for selectively producing isosorbide-5-nitrate Process for selectively producing isosorbide-5-nitrate

1980-01-24

1981-10-27

Miller, Edward A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603474, 424285, C07D30700

Patent

active

042972868

ABSTRACT:
The present invention is related to a new process for selectively preparing isosorbide-5-nitrate (1.4-3.6-dianhydrosorbitol-5-nitrate) by subjecting isomannide (1.4-3.6-dianhydromannitol) in an organic solvent or an aqueous-organic reaction medium to reaction with the equivalent amount of an acid halogenide or the anhydride of a benzene or naphthalene sulfonic acid possibly substituted by lower alkyl, lower alkoxy and/or halogen, of a perfluoro - lower alkane-sulfonic acid, of a lower alkanesulfonic acid or of a perfluoro - lower - alkanoic acid or with the equivalent amount of an acid halogenide of a carbamic acid or of sulphurous acid; subjecting the resulting isomannide-2-ester in the presence of a solvent and possibly with heating, to reaction with an alkali metal salt or an ammonium salt of a benzoic acid possibly substituted by lower alkyl, lower alkoxy and/or halogen or of a lower alkanoic acid; converting the hydroxy group in the 5-position of the resulting isosorbide-2-ester into the nitric acid ester group in manners known per se by reaction with nitric acid; and subjecting the resulting isosorbide-2-ester-5-nitrate to selective hydrolysis and/or reesterification in an organic or aqueous-organic solvent with an alkali metal hydroxide in manners known per se.

REFERENCES:
patent: 3886186 (1975-05-01), Dvonch et al.
patent: 4065488 (1977-12-01), Chou et al.
patent: 4156736 (1979-05-01), Cordes et al.

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