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Study on Synthesis and NMR Characterization of 2,3‐ O ‐Hydroxyethyl Cellulose Depending on Synthesis Conditions
Author(s) -
PetzoldWelcke Katrin,
Kötteritzsch Manuela,
Fenn Dominik,
Koschella Andreas,
Heinze Thomas
Publication year - 2010
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/masy.201000003
Subject(s) - substituent , tetrahydropyran , regioselectivity , chemistry , cellulose , hydroxyethyl cellulose , hydrolysis , polymer chemistry , side chain , nuclear magnetic resonance spectroscopy , surface modification , organic chemistry , ring (chemistry) , catalysis , polymer
The synthesis of hydroxyethyl celluloses with regioselective functionalization in position 2 and 3 starting from triphenylmethyl (trityl) cellulose is described. The effects of reaction conditions upon both the degree of substitution and the distribution of the hydroxyethyl moieties were investigated in detail. The interest was not only focused on regioselective functionalization within the anhydroglucose unit but also on the formation of oxyethylene side chains. To avoid the formation of oxyethylene side chains, 2‐(2‐bromoethoxy)tetrahydropyran was used as etherifying agent in comparison with 2‐bromoethanol. By acidic hydrolysis, both protecting groups – trityl at 6 position and tetrahydropyran at the hydroxyethyl substituent – can be simultaneously cleaved off. The hydroxyethyl celluloses were characterized by one‐ and two‐dimensional NMR spectroscopy in order to determine the substitution pattern.