5-(Chloromethyl)furfural (CMF) is rapidly being established as a renewable platform chemical of great promise. The effects of mass transfer, reaction temperature, Hansen solvent parameters, solvent fraction, and initial glucose concentrations on yields of CMF, 5-(hydroxymethyl)furfural (HMF), 2-(hydroxyacetyl) furan (HAF), levulinic acid (LA), and humic matter were investigated in a two-phase system of 6 M HCl and an organic solvent. The ability of the solvent to extract HMF from the aqueous phase is found to be critical to achieving high CMF yields. Effective solvents must possess at least a small degree of Hansen hydrogen bonding capacity, and a high polarity is beneficial. Yields of CMF and HAF decrease with increasing glucose concentration but the yield of HMF is largely unaffected. The maximum productivity of CMF is achieved at a glucose loading of ca. 1.5 M across all solvent fractions tested. (c) 2015 Elsevier Ltd. All rights reserved.