Synthesis of Nopyl Ethers with Phase Transfer Catalysts

Wang zongde1, xiao zhuanquan2, Chen Jinzhu3

(1 College of Forestry, Jiangxi Agricultural University, Nanchang 330045; 2 College of Chemistry, Jiangxi Normal University, Nanchang 330027; 3 College of Science, Jiangxi Agricultural University, Nanchang 330045)

Abstract Nopyl n-butyl ether and nopyl benzyl ether were synthesized by Williamson reaction of nopol and n-butyl bromide, benzyl chloride respectively, using tetrabutyl ammonium bromide, tetrabutyl ammonium iodide, cytyltrimethyl ammonium bromide, PEG400 and PEG600 as phase transfer catalysts (PTC) respectively, sodium hydroxide as base and benzene as solvent. The result shows tetrabutyl ammonium bromide was the best catalyst with a high transformation ratio of nopol (96.4% and 95.0% respectively). The optimized conditions were as follows, Molar ratio of nopol to hydrocarbon halide to sodium hydroxide to tetrabutyl ammonium bromide was 1:1.2:1.5:0.04, reaction time was 4h and reaction temperature was 80°C. Structure of the both products was confirmed by IR, MS, 1H NMR and 13C NMR spectrometry.
Key words Nopyl n-butyl ether, Nopyl benzyl ether ether, Phase transfer catalysis, Tetrabutyl ammonium bromide


相转移催化合成诺卜基醚类化合物

王宗德1 肖转泉2 陈金珠3
(1江西农业大学林学院 南昌 330045 2江西师范大学化学学院 南昌 330027 3江西农业大学理学院 南昌 330045)

摘要 以诺卜醇(Nopol)、1-溴丁烷和氯化苄为原料，分别以四丁基溴化铵、四丁基碘化铵、十六烷基三甲基溴化铵、PEG400、PEG600为相转移催化剂(PTC)，氢氧化钠水溶液为碱，苯为溶剂，经Williamson醚化反应合成了诺卜基丁基醚和诺卜基苄基醚。四丁基溴化铵效果最好，诺卜醇的最高转化率分别为96.4%和95.0%，最佳合成条件是：n(Nopol):n(RX):n(NaOH):n(Bu4N+Br-)=1:1.2:1.5:0.04，反应时间为4h，反应温度为80°C。两种产物都经IR、MS、1H NMR和13C NMR分析确认。
关键词 诺卜基丁基醚 诺卜基苄基醚 相转移催化 四丁基溴化铵

王宗德 男，31岁，副教授，博士后，主要从事林产化工的教学和科研工作。E-mail:wangzongde@sohu.com
江西省自然科学基金项目(982019)
2002-10-21收稿，2002-12-20修回

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