Syntheses of 3'-formylbenzocrown ethers

Abstract

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

CLC Number:

O621

Cite this article

HOU SHOUJUN;LI SHUMIAN;TIAN BAOZHI;HUANG SHU. Syntheses of 3'-formylbenzocrown ethers[J]. Chin. J. Org. Chem., 1992, 12(4): 424-428.

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3'甲酰基苯并冠醚的合成