3-氯-6-羟基-2-(甲氧基甲氧基)苯甲醛的合成与表征

以2,6-二羟基苯甲醛为原料,通过氯代、醚化两步反应,合成得到3-氯-6-羟基-2-(甲氧基甲氧基)苯甲醛。通过对反应条件优化,确定最佳氯代条件为:n(NCS)∶n(2,6-二羟基苯甲醛)=1.2∶1;甲醇为反应溶剂;反应温度50℃;反应时间16 h条件下,氯代产物收率达到94.8%。最佳醚化条件为:氢化钠用量为n(NaH)∶n(3-氯-2,6-二羟基苯甲醛)=1.5∶1;n(氯甲基甲醚)∶n(3-氯-2,6-二羟基苯甲醛)=1.4∶1,反应室温进行1 h,3-氯-6-羟基-2-(甲氧基甲氧基)苯甲醛(1)收率为39.3%。反应中间体及目标化合物结构通过¹H NMR和ESI-MS进行表征,并通过¹H-¹H NOESY对目标产物进行了表征。

Synthesis and Characterization of 3-Chloro-6-hydroxy-2-(methoxymethoxy)benzaldehyde

3-Chloro-6-hydroxy-2-(methoxymethoxy)benzaldehyde was synthesized from 2,6-dihydr-oxybenzaldehyde through a two-step reaction, involving chlorination and etherification. The reaction conditions were also investigated and the optimal conditions of chlorination were as follows: n(NCS)∶n(2,6-dihydroxybenzaldehyde)=1.2∶1, methanol as solvent at 50 ℃ for 16 h so that the chlorinated product was obtained in a yield of 94.8%. The optimal conditions of etherification were as follows: the dosage of sodium hydride is n(NaH)∶n(3-chloro-2,6-dihydroxybenzaldehyde)=1.5∶1, n(Chloromethyl ether)∶n(3-chloro-2,6-dihydroxybenzaldehyde)=1.4∶1, the reaction was stirred at room temperature for 1 h. 3-Chloro-6-hydroxy-2-(methoxymethoxy)benzaldehyde was then obtained in a yield of 39.3%. The structure of the product and intermediate were identified by ¹H NMR and ESI-MS. The structure of the target compound was also confirmed by ¹H-¹H NOESY.