四氢萘的乙酰化反应研究

Research on Acylation of 1,2,3,4-Tetrahydronaphthalene with Acetyl Chloride

以1,2-二氯乙烷为溶剂,无水三氯化铝为催化剂,通过调整底物的投料比例、反应温度、反应时间以探索四氢萘与过量乙酰氯反应生成3,6-二乙酰基-1,2-二氢萘的最优反应条件。结果表明在AlCl3/CH2ClCH2Cl体系中,四种底物与乙酰氯以物质的量之比为1:3的比例投入,室温反应1h,是得到相应产物的最优反应条件。优化后的反应条件具有实验条件温和,反应时间短,原料可以回收再利用等优点。根据产物中的共轭不饱和酮骨架结构,提出了傅克酰基化、Nenitzescu还原酰基化的串联反应机理。

With 1,2-dichloroethane as the solvent and water-free Alchlor as the catalyst,this paper probes into the best interaction conditions of 1,2,3,4-tetrahydronaphthalene and excess of acetyl chloride to produce 3,6-diacetyl-1,2-dihydronaphthalenes via adjusting the material input ratio of substrates,reaction temperature and time.The results indicate that in AlCl3/CH2ClCH2Cl system,four substrates reacted with acetyl chloride with the material input ratio of 1：3 molar and with greenhouse reaction for 1h can produce the optimum reaction conditions for the corresponding products.The optimized reaction conditions are characterized by moderate experiment conditions,short reaction time and recoverable and reasable raw materials.For the first time,a cascade Lewis acid catalyzed Friedel-Crafts acylation and Nenitzescu reductive acylation mechanism is proposed according to the formation of the conjugated unsaturated ketone skeleton in the products in this paper.