Synthesis of new phenolic type acyclic crown ethers and derived dibenzocrown ethers

Abstract

In the presence of NaH and in DMF, the acyclic crown ethers 1a and 1b were synthesized by the reaction of di-or triethyleneglycol ditosylate and o-methoxymethoxybenzyl alcohol, which was obtained from salicylaldehyde via the protection of the hydroxyl group with chloromethyl methyl ether followed by the reduction of the formyl group with NaBH4. The hydrolysis of 1a and 1b with dilute hydrochloric acid provided the diphenolic type acyclic crown ethers 2a and 2b respectively in good yield. By using 2a as the intermediate, syn- dibenzo-20-crown-6(3) was produced by reaction with diethyleneglycol ditosylate and NaH in DMF solution, and 17-hydroxydibenzo-18-crown- 5(4) was obtained by reaction with epichlorohydrin and NaOH in aqueous solution.

Key words: PHENOLS, SODIUM BOROHYDRIDE, SALICYLIC ALDEHYDE, SODIUM HYDRIDE, CROWN ETHER, OPEN CHAIN COMPOUND, SODIUM HYDROXIDE, EPOXYCHLOROPROPANE

CLC Number:

O621

Cite this article

MENG JIE;TIAN BAOZHI;HUANG SHU. Synthesis of new phenolic type acyclic crown ethers and derived dibenzocrown ethers[J]. Chin. J. Org. Chem., 1996, 16(3): 253-257.

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