Selective monoetherification and monoesterificatton of diols and diacids under phase-transfer conditions

Jaime de la Zerda*, Gabriela Barak, Yoel Sasson

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

Research on the selectivity of etherlfication reactions of diols and esterification reactions of diacids by alkyl halides under phase-transfer catalysis has shown that under such conditions, selectivity of monoetherification increases in the order prim < sec < tert diols, though overall yield of monoether decreases from sec to tert diols. Monoesterification of diacids was accomplished with a high degree of selectivity. Optimal extraction of diols and diacids was found to correspond in general to chain lengths of around 5 carbons. This could mean that the complex formed between the catalyst and the anion to react is stabilized for certain carbon lengths by inner solvation in virtue of its spatial conformation.

Original languageEnglish
Pages (from-to)1533-1536
Number of pages4
JournalTetrahedron
Volume45
Issue number5
DOIs
StatePublished - 1989

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