Synthesis Of 4-Alil-6- (Hydroxymethyl) -2-Methody Phenol Compounds from Eugenol Through Mannich Reaction Followed Methylation with Methyl Iodide and Subtitution Using NaOH
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引用次数: 1
Abstract
Eugenol derivative compound 4-allyl-6-hydroxymethyl-2-methoxy phenol was synthesized through Mannich reaction, methylation, dan nucleophilic substitution. Mannich reaction was carried out by reacting eugenol, formaldehyde 37%, and dimethylamine 40 % in reflux condition with n-heptane solvent at temperature 98o-100oC for 10 hours produced 4-allyl-6-(dimethylamino)methyl-2-methoxy phenol with yield of 83 %. The formation of dimethylaminomethyl group supported by C-N stretching vibration at 1246,16 cm-1 and ion molecule peak at 221 in GC-MS analysis. Methylation of 4-allyl-6-(dimethylamino)methyl-2-methoxy phenol was carried out with methyl iodide in ethanol solvent produced 6-((N-iodo-N-methyl-N-methyl-N-methylamino) methyl)-4-allyl-2-methoxy phenol in solid form, which then purified by recrystallization with 78,15 % yield. 4-allyl-6-(hydroxymethyl)-2-methoxy phenol was synthesized by nucleophilic substitution reaction of 6-((N-iodo-N-methyl-N-methyl-N-methylamino)methyl)-4-allyl-2-methoxy phenol with sodium hydroxide in reflux condition then purified by coloum chromatography gave liquid compound with yield of 65,05%. The formation of hydroxymethyl group supported by OH vibration at 3433,9 cm-1 and ion molecule peak at 194 in GC-MS analysis show the relative molecular mass of synthesized product.
通过曼尼希反应、甲基化、亲核取代合成了丁香酚衍生物4-烯丙基-6-羟甲基-2-甲氧基苯酚。以丁香酚、甲醛37%、二甲胺40%为原料,在正庚烷溶剂回流条件下,在98 ~ 100℃下反应10小时,得到4-烯丙基-6-(二甲胺)甲基-2-甲氧基苯酚,收率为83%。在气相色谱-质谱分析中,C-N在1246、16 cm-1处的拉伸振动和离子分子峰221处支撑二甲氨基甲基的形成。用碘化甲酯在乙醇溶剂中甲基化4-烯丙基-6-(二甲氨基)甲基-2-甲氧基苯酚,得到6-(n -碘- n -甲基- n -甲基- n -甲氨基)甲基)-4-烯丙基-2-甲氧基固体苯酚,再通过重结晶纯化,收率为78.15%。以6-((n -碘- n -甲基- n -甲基- n -甲氨基)甲基)-4-烯丙基-2-甲氧基苯酚为原料,在回流条件下经亲核取代反应合成4-烯丙基-6-(羟甲基)-2-甲氧基苯酚,并经柱层析纯化,得到得率为65,05%的液相化合物。在气相色谱-质谱分析中,OH振动在3433,9 cm-1处支撑形成的羟基甲基和离子分子峰在194处显示了合成产物的相对分子质量。