METHOD OF SYNTHESIS OF DERIVATIVES OF O-CHLOROMETHYLPHENYL-GLYCOXYLIC ACID Russian patent published in 2001 - IPC

FIELD: organic chemistry, chemical technology. SUBSTANCE: invention relates to method of synthesis of compound of the formula (I) where X means radical which is inert under reaction conditions; m = 0; R₃ means hydrogen atom, CH₃,CH₂F or CHF₂; Y means the group OR₄N(R₅)₂ or N(CH₃)OCH₃; R₄ and R₅ each and independently each of other mean hydrogen atom or C₁-C₈-alkyl, or (R₅)₂ in common with nitrogen atom to which they are bound form 5- or 6-membered unsubstituted or substituted ring in accordance with: (a) interaction of compound of the formula (II) where X and m have values indicated for the formula (I) and R₁ and R₂ each and independently each of other mean C₁-C₆-alkyl, C₁-C₆-alkenyl, C₁-C₆-alkoxyalkyl or C₃-C₆-cyclo-alkyl, or R₁ and R₂ in common with nitrogen atom form unsubstituted or substituted 6- or 7-membered ring which except for said nitrogen atom can involve additional nitrogen atom with lithium-organic compound of the formula (III) Li-R₇ (III) where R₇ means organic anion-active radical and reaction is carried out in aprotonic solvent; (b) interaction of obtained lithium complex with compound of the formula (IV) Y₁-CO-CO-Y₁ where each of substitutes Y₁ can be similar or different and mean the group OR₄,N(R₆)₂ or N(CH₃)OCH₃; R₄ means C₁-C₈-alkyl; R₆ means C₁-C_8/ -alkyl or (R₆)₂ in common with nitrogen atom to which they are bound form 5- or 6-membered unsubstituted or substituted ring to yield the compound of the formula (V) ; (c) said compound in any order in (1) is subjected for formation of oximes by reaction with O-methylhydroxylamine or hydroxylamine followed by methylation, fluoromethylation or difluoromethylation; in (2) said compound is subjected for interaction with chloroformic acid ester. Invention proposes also method of synthesis of compound of the formula (V) in accordance with said steps (a) and (b), method of synthesis of compound of the formula (I) from compound of the formula (V) in accordance with said steps in (1) and (2) and compound of the formula (V). The proposed methods provide the available novel way of synthesis of microbiocides of methoxyiminophenylglyoxylic acid order in combination with easy availability of parent substances and good resolution of steps to be proposed. EFFECT: improved method of synthesis, good yield of substances. 17 cl, 13 ex