Syntheses of monohydroxy benzyl ethers of polyols: tri-O-benzylpentaerythritol and other highly benzylated derivatives of symmetrical polyols.
Symmetrical polyols can be converted into benzyl ethers with one free hydroxyl group in good yield by reaction of the monodibutylstannylene acetal with excess benzyl bromide in the presence of tetrabutylammonium bromide and diisopropylethylamine in xylene. The reaction pathway involves initial benzylation of the dibutylstannylene acetal to give benzyl and bromodibutylstannyl ethers; if a hydroxyl group remains unsubstituted, the latter ether ring closes and reacts further.
Al-Mughaid
Hussein
H
Department of Chemistry, Dalhousie University, Halifax, NS, Canada B3H 4J3.
Grindley
T Bruce
TB
D001555:Benzene Derivatives / Q000138:chemical synthesis; D004896:Erythritol; D011108:Polymers / Q000138:chemical synthesis*
D001555:Benzene Derivatives; D011108:Polymers; C024617:polyol; D004896:Erythritol