Synthesis of Di-areno-14-crown-4-diols and separation of their isomers

Abstract

With lithium hydroxide as both the base and template agent, the nucleophilic substitution reaction of epoxide I with catechol, 4-tert-butylcatechol and 2,3-naphthalenediol in tert-butanol was investigated. Three types of diareno-14-crown-4-diols were synthesized. The three pairs of cis- and trans-diols were separated by chromatog. and identified by IR, 1H, NMR, mass spectra and elemental anal., resp. This new method afforded a simple and convenient synthetic route to sym., unsym. diareno-14-crown-4-diols or other hydroxy crown ethers.

Key words: INFRARED SPECTROPHOTOMETRY, SEPARATION, NAPHTHALENE P, MASS SPECTROGRAPHY, ISOMER, ETHER, BENZENEDIOL, CROWN ETHER COMPOUNDS, BUTANOL, PROTON MAGNETIC RESONANCE SPECTROMETRY

CLC Number:

O621

Cite this article

YU ZONGYUAN;BARISCH, R.A. Synthesis of Di-areno-14-crown-4-diols and separation of their isomers[J]. Chin. J. Org. Chem., 1992, 12(2): 146-150.

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