ALKYLATION OF PENTAERYTHRITOL BY PHASE-TRANSFER CATALYSIS 2. Crucial Effect of the Aqueous Sodium Hydroxyde Solution

Article abstract of DOI:10.1016/S0040-4020(01)81699-9

The mechanistic aspects of the alkylation of pentaerythritol (2-2'-bis(hydroxymethyl)-1,3-propanediol) (PE) by phase-transfer catalysis have been investigated.The dramatic effect of an excess and renewal of sodium hydroxide solutions on the one hand, and the solubility of the PT catalyst in the organic phase on the other, argue that the selectivity of this reaction appears to be controlled almost completely by the possible protonation of the sodium form of the alkoxide anion of PE (4).This protonation depends on the assumption that water molecules are present in the PT medium, and it based upon the observation that this PT medium is actually a three liquid-layer system.As the unusual layer (catalyst layer) may be readily hydrated, the concentrated sodium hydroxide solution can be no longer considered as an unquestionable desiccant.