5,5-二甲基-5,6,7,8,9,10-六氢蒽二酚二乙酸酯的合成研究

Synthesis of 5,5-Dimethyl-5,6,7,8,9,10-Hexahydroanthracene-1,4-Diyldiacetate

以月桂烯和对苯醌为起始原料,首先通过Diels-Alder反应得到了蒽二酚,进一步酯化合成了蒽二酚二乙酸酯.采用元素分析、红外光谱、1H NMR、13C NMR等手段对实验产物进行了鉴定,确证最终产物为5,5-二甲基-5,6,7,8,9,10-六氢蒽-1,4-二酚二乙酸酯.对产物进行了HPLC分析,产物纯度达到99.15%.探讨了酰化反应的催化剂种类、催化剂用量、反应温度、反应时间和反应物物质的量之比对产物收率的影响,并采用正交试验优化了反应工艺,得出最佳的工艺条件为:蒽二酚用量为0.025 mol,n(乙酸酐)∶n(蒽二酚)=8∶1,催化剂为吡啶,用量为蒽二酚质量的10%,反应温度40℃,反应时间6 h.在上述条件下,产物得率为93.4%.

The diacetyl anthrahydroquinone was prepared from anthrahydroquinone and acetic anhydride. The anthrahyd- roquinone was synthesized with myrcene and p-benzoquinone as raw materials via Diels-Alder reaction. The structure of the product was identified by elemental analysis, IR and NMR and it was confirmed to be 5,5-dimethyl-5,6,7,8,9,10- hexahydroanthracene-1,4-diyldiacetate. The purity was shown to reach 99. 15% by HPLC. The acylation reaction effects of different catalyst amounts, reaction temperature, reaction time and molar ratio of acetic anhydride and anthrahydroqui- none on the yield were discussed. Then the synthesis technology was optimized by orthogonal experimental method. The optimum reaction conditions are as follows ： anthrahydroquinone is 0. 025 mol, n （ acetic anhydride） ： n （ anthrahydroqui- none） = 8：1 ; pyridine as catalyst; the amount of catalyst is 10% weight of anthrahydroquinone; reaction temperature 40℃ and reaction time 6 h ; under these conditions, the yield of product is 93.4%.