Alkylation of Pentaerythritol and Trimethylolpropane, Two Very Hydrophilic Polyols, by Phase-Transfer Catalysis.

Article abstract of DOI:10.1021/jo00218a010

Two very hydrophilic polyols, pentaerythritol <2,2'-bis(hydroxymethyl)-1,3-propanediol (PE)> and trimethylolpropane <2-ethyl-2-(hydroxymethyl)-1,3-propanediol (TMP)>, can be etherified in good yields by phase-transfer catalysis with allyl chloride or heptyl bromide as alkylating agents.Ion pairs solubilities, lipophilicities of catalysts, and nature of the reaction products which are key factors in achievement of this PTC reaction are discussed.