Reaction in hot water

16 January 2015 - Orgo

The latest reaction inducted in the Chemical Reaction Database (CRD) is lifted from an article by Feng-Zhi Zhang et al. (DOI) about intramolecular etherification by activated alcohols. Is hot water as advertised in the title an efficient reaction promotor? Or is water just a terrible solvent given that the reaction requires extensive heating for it to work? Given that the reactant is a liquid at 100°C, could one actually do away with the water and make it a no-solvent reaction? The reaction scale: 13 mg of reactant in 50 ml of water also raises concerns. On the other hand, many points for carefully listing the systematic names of the newly synthesised compounds, essential as raw CRD input.
reaction in hot water.PNG