METHOD OF SYNTHESIS OF 1,6-DIARYL-3,4-DIHYDROXY-2,4-HEXADIENE-1,6-DIONES

摘要

FIELD: organic chemistry. SUBSTANCE: method of synthesis of 1,6-diaryl-3,4-dihydroxy-2,4-hexadiene-1,6-diones of the general formula 4-R′C₆H₄-COOH = C(OH)C(OH) = CHCO-C₆H₄R″-4 where R′ = H; CH₃; R″ = Br; R′ = R ″ = Cl involves the interaction of 5-aryl-2,3-dihydro-2,3-furandione of the general formula where R′ as indicated above with organic reagent at increased temperature in the medium of organic solvent. Organic reagent is aroyldimethylenetriphenylphosphorane of the general formula C₆H₅)₃P = CHCOC₆H₄R″-4 where R² as indicated above which interacts with 5-aryl-2,3-dihydro-2,3-furandiones at the mole ratio 1:1, respectively, at 70-80 C using benzene as an organic solvent and 5-aryl-2-aroylmethylene-2,3-dihydro-3-furanone of the general formula is synthesized where R′ and R² have values indicated above. Synthesized compound is reacted then with hydrochloric acid at the mole ratio 1:4, respectively, at 40-50 C using acetone as an organic solvent. The yield of the end product under these conditions is 95%. EFFECT: increased yield, simplified technology. 1 tbl