关键词: 二甲基甲酰胺, 苯甲醛 P, 氢化钠, 苯甲醛 P, 多甘醇, 冠式化合物, 苯磺酸 P, 碳酸钾, 磺酸酯

3'-Formylbenzocrown ethers I (n = 1, 2, 3) and 3',3''-diformyldibenzocrown ethers II (n = 1, 2, 3) were synthesized from 2,3-dihydroxybenzaldehyde with polyethylene glycol ditosylates and NaH in DMF (method A) or polyethylene glycol dichlorides and K2CO3 in DMF (method B) resp. By method A, the acyclic intermediates III (n = 1, 2) were also isolated from the reaction products. II (n = 1) prepared by method B was separated into the syn and anti isomers by further column chromatog. The cause concerning the reluctance of the reactions and the poor yields of the products is discussed in detail. It may be due to the presence of the formyl group on the benzene ring which would provide the neighboring hydroxyl group with a stronger acidity and then its anion with a weaker nucleophilicity.

Key words: BENZALDEHYDE P, BENZALDEHYDE P, SODIUM HYDRIDE, CROWN ETHER COMPOUNDS, BENZENESULFONIC ACID P, POTASSIUM CARBONATE, SULFONIC ACID ESTER, DIMETHYLFORMAMIDE