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The Reaction Of Phenol And Trichloro Acetyl Chloride, Substituted Amino Phenol Phloroglucinol Synthesis Research

Posted on:2006-05-12Degree:MasterType:Thesis
Country:ChinaCandidate:X F YuanFull Text:PDF
GTID:2191360155459754Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
This dissertation consisits of two parts:Part Ⅰ:The friedel-crafts reaction of trichloroacetyl chloride and substituted phenols hasbeen discussed. Firstly, substitutedα,α,α-trichloroacetylphenols were synthesizedthrough the reaction between trichloroacetyl chloride and p-chlorophenol,p-methylphenol, p-bromophenol, 2,6-dimethylphenol ,phenol, m-fluorophenol,4-phenyl phenol respectively. Substituted hydroxylarylamides were produced by thereaction of α,α,α-trichloroacetylphenol with NH3. Hydroxyl aryl amides weredehydrated to obtain hydroxybennitrils. α,α,α-trichloroacetylphenol reactedwith the aqueous solution of NaOH, then PH of the mixture was adjusted byadding HCl and finally respective substituted hydroxylbenzoic acids were obtained.We found an easy and convenient way to introduce the carboxyl and cyano. Secondly,azoic compounds were synthesized through the reaction betweendiazobenzenesulfonic acid and p-methylphenol, 2,6-dimethylphenol, m-methylphenol,p-bromophenol, o-methylphenol, phenol, p-chlorophenol, p-methoxylphenolrespectively. Azoic compounds were reduced to corresponding substitutedaminophenol by SnCl2. All the compounds were characterized by IR,1HNMR,UVand element analysis.Part Ⅱ:1,3,5-trimethoxylbenzene and phloroglucin are the intermediates of chemicaland medicine industry. 1,3,5-trimethoxylbenzene and phlorog lucin were producedunder the optimum condition. H2O2 was titrated to the mixture of benzenamine andHBr solutions to produce tribromo-benzenamine, which was further underwent diazoreaction to obtain 1,3,5-tribromobenzene. 1,3,5-trimethoxylbenzene was synthesizedthrough 1,3,5-tribromobenzene and sodium methylate with CuCl as catalyst.Phloroglucin was finally prepared by the hydrolysis of 1,3,5-trimethoxylbenzene inthe HBr solution for 24 hours. The synthesis method has several advantages as...
Keywords/Search Tags:the Friedel-Crafts Reaction, Trichloroacetyl chloride, Alkaline hydrolysis, Aminolysis, reduction, diazo coupling reaction, phloroglucin
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