Efficient synthesis of C-pivot lariat ethers. 2-(Alkoxymethyl)-1, 4, 7, 10, 13, 16-hexaoxacyclooctadecanes

SJ Jungk, JA Moore, RD Gandour

Index: Jungk, Steven John; Moore, Jane Ann; Gandour, Richard David Journal of Organic Chemistry, 1983 , vol. 48, # 7 p. 1116 - 1120

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Citation Number: 37

Abstract

Reaction of an alcohol with excess (chloromethy1) oxhane (epichlorohydrin) produces the desired (alkoxymethy1)-oxirane (2) in excellent yield (Table I). Treatment of 2 with excess 3, 7-dioxaoctane-l, 8-diol (triethylene glycol) in the presence of catalytic amounts of NaH affords the 1-(alkoxymethyl)-3, 6, 9-trioxaundecane-l, ll-diol (3) in surprisingly high yields. It has been found that 3 can be easily isolated from triethylene glycol by continuous ...