Polyethers of cinnamaldehyde acetal. Part 1: Williamson etherification of 1,n-dibromoalkanes with methyl 4,6-O-cinnamylidene-α-d-glucopyranoside

A series of aliphatic (C4-C12) diethers of methyl 4,6-O-cinnamylidene-α-d-glucopyranoside (1) were prepared as model compounds. Polycondensation of 1 and 1,n-dibromoalkanes (2) catalyzed by K2CO3/KI or KOH/phase-transfer catalyst systems was performed in solvents (DMF/butyl acetate, DMSO). Reactions carried out in the presence of KOH/TBAC or KOH/18-crown-6 yield the complex mixture of products due to side reactions. IR, 1H and 13C NMR and ESI-MS were used to study the details of the polymer structure.