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Synthesis of hydroxymethyl-21-crown-7 and hydroxymethyl-24-crown-8

✍ Scribed by Bronislaw Czech; Anna Czech; Richard A. Bartsch

Book ID
104217097
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
128 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

ZJiWXW

Reactions of 3,6-dioxa-4-(benzyloxymethyl)-l,&octanediol with appropriate ditosylates followed by hydrogenolysis produce two new functionalized crown ethers.

Hydroxymethyl crown ethers are versatile intermediates for further structural modification' and for the formation of polymer-supported crown ethers.

2 Although hydroxymethyl derivatives of 12-crown-4, 15-crown-5 and M-crown-6 are well-known,3 the preparation of similarlyfunctionalized forms of larger-ring crown ethers has not been reported.

In this paper we describe the first syntheses of hydroxymethyl-21-crown-7 (L) and hydroxymethyl-24-crown-8 (2). Both preparations utilize the accessible4 3,6-dioxa-4-(benzyloxymethyl)-1,8-octanediol (A) as a key synthetic intermediate.

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