METHOD FOR SYNTHESIS OF ASPIRIN NITROXYMETHYLPHENYL ESTERS AND ITS DERIVATIVES Russian patent published in 2004 - IPC

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention describes a method for synthesis of aspirin nitroxymethylphenyl esters and its derivatives. Invention describes a method for preparing aspirin (nitroxymethyl)phenyl esters and its derivatives of the formula R-COOH with types of radicals of the following formula: (Ia)

and (Ib)

wherein: R₁ means group OCOR₃ wherein R₃ means methyl, ethyl or linear or branched (C₃-C₅)-alkyl; R₂ means hydrogen atom; n1 = 0. Above mentioned method for synthesis involves the following stages: (1) reaction between R-C(O)-X₁A wherein X₁ means Cl, Br; R means radical determined above with hydroxybenzaldehyde isomer in the presence of a base to yield (carbonyl)phenyl ester (I); (2) reduction of aldehyde group in (carbonyl)phenyl ester to yield (hydroxymethyl)phenyl ester; (3) reaction between (hydroxymethyl)phenyl ester of the formula (II) with: (a) SOX₂ wherein X means halogen atom taken among Cl and Br and (b) with tosyl chloride or mesyl chloride; (4) reaction between ester prepared on the previous stage with inorganic nitrate salt wherein its metal cation belongs to the group IB or IIB to yield (nitroxymethyl)phenyl ester. Also, invention describes aspiring derivatives (hydroxymethyl)phenyl ester of the formula R-COOH, 2-(acetyloxy)benzoic acid 2-(nitroxymethyl)phenyl ester and 2-(acetyloxy)benzoic acid 4-(nitroxymethyl)phenyl ester. Invention provides simplifying process in preparing end products and good yields of end products.

EFFECT: improved method for synthesis.

7 cl, 3 ex