Synthesis and alkali-cation complexing properties of 12-crown-4 derivatives.

T Miyazaki, S Yanagida, A Itoh, M Okahara

Index: Miyazaki, Takeshi; Yanagida, Shozo; Itoh, Akira; Okahara, Mitsuo Bulletin of the Chemical Society of Japan, 1982 , vol. 55, # 7 p. 2005 - 2009

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Citation Number: 51

Abstract

Benzyloxymethyl-12-crown-4, a precursor of hydroxymethyl-12-crown-4, is prepared in an excellent yield by the reaction of 3-benzyloxy-1, 2-propanediol with 1, 8-dichloro-3, 6- dioxaoctane in the heterogeneous t-BuOLi/t-BuOH/LiBr· 2H 2 O reaction system. The hydrogenolysis in the presence of p-toluenesulfonic acid leads to a good yield of hydroxymethyl-12-crown-4. The sandwich-type 2: 1 complexation with Na+ of 12-crown-4 ...