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以3,5-二甲氧基苯甲醛和4-甲氧基苯乙酸为原料,经Perkin反应、脱羧和脱甲基/异构化3步反应,合成了白藜芦醇,总收率62.5%。对脱羧反应条件的溶剂、催化剂和碱进行了研究,并寻找脱甲基异构化的方法。喹啉/Cu/NaOH体系脱羧反应产率最高,达80.5%,且反应时间缩短;在相同的产率下,二甲亚砜/CuBr/NaOH体系反应温度可降至180℃。用三溴化硼、无水三氯化铝均可脱甲基/异构化,产率分别为86.1%和62.4%。结果表明:在脱羧反应体系中加入强碱,用三溴化硼脱甲基/异构化,结果较好。
Starting from 3,5-dimethoxybenzaldehyde and 4-methoxyphenylacetic acid, three steps of Perkin reaction, decarboxylation and demethylation / isomerization were used to synthesize resveratrol with the total yield of 62.5 %. The solvent, catalyst and base of the decarboxylation reaction conditions were studied, and the method of demethylation was investigated. The yield of decarboxylation of quinoline / Cu / NaOH system was the highest (80.5%), and the reaction time was shortened. The reaction temperature of dimethyl sulfoxide / CuBr / NaOH system could be reduced to 180 ℃ under the same yield. With boron tribromide, anhydrous aluminum trichloride can be demethylated / isomerized, the yield was 86.1% and 62.4%. The results showed that adding strong base to the decarboxylation reaction system and demethylating / isomerizing with boron tribromide gave better results.