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Synthesis Aromatic Ketones By Friedel-Crafts Acylation Reaction

Posted on:2005-11-18Degree:MasterType:Thesis
Country:ChinaCandidate:Y H GuoFull Text:PDF
GTID:2121360122471480Subject:Applied Chemistry
Abstract/Summary:PDF Full Text Request
2-chloroacetophenone and its derivatives are important intermediates in organic synthesis, applied in various areas of the fine chemical industry, such as pharmaceutical, pesticide, plastic, liquid crystals. Asymmetric reduction of acetophenone derivatives preparing chiral aromatic alcohol has become a new focus of study. Friedel-Crafts acylation is important and fundamental organic reactions for preparing aromatic ketones. The aim of this work is to prepare 2-chloroacetophenone derivatives.Studying acylation of chlorobenzene preparing 2,4-dichloroacetophenone, an optimum processing condition of the synthesis of mono-substituted 2 -acetophenone derivatives was obtained. By the reaction of mono-substituted benzene, chloroacetyl chloride and aluminum chloride anhydrous in mole ratio of 1:1.2:1.8 with carbon disulfide as solvent at 15-20℃ for about 4h, we prepared 2-chloroacetophenone, 2-chloro-4-fluroacetophenone, 2 ,4-dichloroacetophenone, 2 -chloro-4-bromoaceto-phenone, 2-chloro-4-methylacetophenone, 2-chloro-4-ethylacetophenone, 2-chlo-ro-4-methoxyacetophenone, 2 -chloro-4-phenylacetophenone.Studying acylation of 1,3-dichlorobenzene preparing 2,2,4-trichloro-acetophenone, an optimum processing condition of the synthesis of di-substituted 2 -acetophenone derivatives was obtained. By the reaction of di-substituted benzene, chloroacetyl chloride and aluminium chloride anhydrous in mole ratio of 1:1.2:1.7 without solvent at 50-55℃ for about 4h, we prepared 2,2,4-trichloroacetophenone, 2 -chloro-2,4-difluroacetophenone, 2 ,3,4-trichloroacetophenone, 2 -chloro-2,4-dime-thylacetophenone, 2-chloro-3,4-dimethylacetophenone,.3-chloro-l-phenylacetone and 3-chloro-l-(α -thiophene)acetone were prepared, The yield and the purity of the products were high.All of these compounds were identified by IR, their melt point and solubility were measured.
Keywords/Search Tags:Friedel-Crafts acylation, synthesis, aluminium chloride anhydrous, chloroacetylchloride, 3-chloropropionyl chloride, 2-chloroacetophenone derivatives, 3-chloro-l-phenylacetone, 3-chloro-l-( α -thiophene)acetone
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