Abstract
An efficient procedure for the regioselective synthesis of secondary alcohol alkoxylates from 2,2,4-trimethyl-1,3-pentanediol (TMPD) is described. TMPD was reacted with propylene oxide followed by ethylene oxide in the presence of a catalytic amount of alkali metal hydroxide to form secondary alcohol alkoxylates. Instead of a mixture of compounds resulting from the reaction of TMPD and propylene oxide, the primary hydroxyl group of the TMPD reacted to form predominantly 2,2,4-trimethyl-3-hydroxypentylpropoxylate as the major product. On further ethoxylation the less hindered secondary hydroxyl group of the 2,2,4-trimethyl-3-hydroxypentylpropoxylate reacted predominantly. 13C NMR indicated that the secondary hydroxyl group (96.2 mol%) of TMPD remained unreacted during alkoxylation.
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Rahman, M.A., Su, BM., Band, E. et al. Regioselective Alkoxylation of 2,2,4-Trimethyl-1,3-pentanediol. J Surfact Deterg 14, 333–338 (2011). https://doi.org/10.1007/s11743-011-1257-4
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DOI: https://doi.org/10.1007/s11743-011-1257-4