METHOD OF SYNTHESIS OF HALOGEN-O-HYDROXY-DIPHENYL COMPOUNDS AND ACYL COMPOUNDS Russian patent published in 2002 - IPC

FIELD: organic chemistry, chemical technology. SUBSTANCE: invention relates to novel method of synthesis of halogen-o-hydroxydiphenyl compounds of the formula (1) where X means +O- or -CH₂-; m = from 1 to 3; n = 1 or 2 which are used for protection of organic materials from microorganisms and to novel acyl compounds of the formula (8) that are intermediate substances where R means unsubstituted C₁-C₈-alkyl or substituted with 1-3 halogen atoms or hydroxy-group; or unsubstituted C₆-C₁₂-aryl or C₆-C₁₂-aryl substituted with 1-3 halogen atoms, C₁-C₅-alkyl or C₁-C₈-alkoxy-group. Method of synthesis of compounds of the formula (1) involves four stages. On the first stage corresponding diphenyl compound of the formula (4) is chlorinated with gaseous chlorine mainly and in the presence of propyl sulfide and the equimolar amount of aluminium chloride preferably. On the second stage synthesized corresponding chlorinated compound of the formula (5) is acylated with acetyl chloride mainly by Friedel-Crafts reaction in the presence of Lewis acid, for example, aluminium chloride in the equimolar ratio of acetyl chloride and aluminium chloride usually in the presence of halogenated solvent with the following possible chlorination of synthesized product after acylation. It is possible to carry out acylation and possible chlorination reactions in a single reactor. On the third stage synthesized acyl compound of the formula (6) where values of substitute R are indicated above is oxidized with as a rule with mixture of maleic anhydride, complex urea-hydrogen peroxide and acetic acid as solvent. On the fourth stage synthesized oxidized compound of the formula (7) where values of substitute R are indicated above is hydrolyzed. Method ensures to inhibit undesirable by-side reactions. EFFECT: improved method and efficiency of method. 15 cl, 8 tbl