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3,4,5-三甲氧基苯胺的合成研究

Synthesis of 3,4,5-Trimethoxyaniline
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摘要 以3,4,5-三甲氧基苯甲酸为原料,经酰氯化、酰胺化和霍夫曼重排三步反应,制备了3,4,5-三甲氧基苯胺。采用FT-IR、GC-MS等手段对3,4,5-三甲氧基苯胺结构进行了表征。同时得到了中间产物3,4,5-三甲氧基苯甲酰氯的最优合成工艺条件为:三氯化磷与3,4,5-三甲氧基苯甲酸物质的量之比0.65∶1,甲苯为溶剂,甲苯与3,4,5-三甲氧基苯甲酸2.83∶1(mL∶g),反应温度80℃,反应时间3 h;中间产物3,4,5-三甲氧基苯甲酰胺的最优合成工艺条件为:氨水与3,4,5-三甲氧基苯甲酰氯物质的量之比4∶1,反应温度-5~0℃,反应时间30 min;3,4,5-三甲氧基苯胺的最优合成工艺条件为:NaOH与3,4,5-三甲氧基苯甲酰胺物质的量之比为9∶1,Br2与3,4,5-三甲氧基苯甲酰胺物质的量之比1.15∶1,重排反应温度40℃,重排反应时间20 min,脱羧温度85℃,脱羧时间1 h,去离子水为溶剂。产物得率66.8%,熔点112.5~113.5℃,纯度99.0%。 3,4,5-trimethoxyaniline was synthesized from 3,4,5-trimethoxybenzioc acid. 3,4,5-trimethoxyaniline through chlorin- ation of 3,4,5-trimethoxybenzioc acid, amidation of 3,4,5-trimethoxybenzoyl chloride and Hofmann rearrangement reaction of 3,4,5-trimethoxybenzamide. The structure of 3,4,5-trimethoxyaniline was determined by FT-IR and GC-MS spectra. The optimal reaction conditions of 3,4,5-trimethoxybenzoyl chloride was as follows: n (phosphorus trichloride) : n (3,4,5-trimethoxybenzioc acid) = 0.65 : 1, toluene as the solvent, v (toluene) : n (3,4,5-trimethoxybenzioc acid) = 0.6 : 1 ( L : mol), reaction temperature 80 ~C, reaction time 3 h. The optimal reaction conditions of (3,4,5-trimethoxybenzamide) was as follows: n(ammonia) : n(3, 4,5-trimethoxybenzoyl chloride) = 4: 1, reaction temperature -5 -0 ~C, reaction time 30 min. The optimal reaction conditions of (3,4,5-trimethoxyaniline) was as follows : n(NaOH) : n (3,4,5-trimethoxybenzamide) = 9 : 1, n( Br2 ) : n( 3,4,5-trimethoxy- benzamide) = 1.15 : 1, rearrangement reaction temperature 40 ~C, rearrangement reaction time 20 min, decarboxylation tempera- ture 85 ~C, decarboxylation time 1 h, deionized water as the solvent. Yield of obtained product was 66.8 %, m.p. 112.5 - 113.5 C, purity of obtained product was 99.0 %.
出处 《林产化学与工业》 EI CAS CSCD 北大核心 2013年第4期93-100,共8页 Chemistry and Industry of Forest Products
基金 林业公益性行业科研专项(201104015) 国家自然科学基金资助项目(31170538)
关键词 3 4 5-三甲氧基苯甲酸 Hofmann重排 3 4 5-三甲氧基苯胺 3,4,5-trimethoxybenzoic acid Hofamnn rearrangement 3,4,5-trimethoxyaniline
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