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将水杨醛与碱和氯甲基甲基醚反应,再经过NaBH_4还原。即制得邻(甲氧基甲氧基)苯甲醇。然后将其在DMF中与NaH和二(或三)甘醇二对甲苯磺酸醑反应,得开链冠醚1a和1b。1a和1b经稀酸水解。即脱保护而分别生成新的酚型开链冠醚2a和2b。用2a与二甘醇二对甲苯磺酸酯和NaH在DMF溶液中反应,合成顺型二苯并-20-冠-6(3);而2a与环氧氯丙烷在NaOH水溶液中反应,则合成了17-羟基二苯并-18-冠-5(4)。
Salicylaldehyde and base and chloromethyl methyl ether reaction, and then NaBH_4 reduction. Ortho (methoxy methoxy) benzyl alcohol. This is then reacted with NaH and di (or tri) ethylene glycol bis (p-toluenesulfonate) in DMF to give the crown ethers 1a and 1b. 1a and 1b are hydrolyzed by dilute acids. Ie, deprotection to generate new phenolic open-chain crown ethers 2a and 2b, respectively. Cis-dibenzo-20-crown-6 (3) was synthesized by the reaction of 2a with diethylene glycol bis-toluenesulfonate and NaH in DMF solution. When 2a reacted with epichlorohydrin in NaOH solution, 17-hydroxy dibenzo-18-crown-5 (4) was synthesized.