4-Hydroxybenzaldehyde → 4-(2-Bromoethoxy)Benzaldehyde

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Reaction Steps

In order to prepare a benzaldehyde conjugated alginate, a few appropriate precursors are first synthesized. 4-(2-bromoethoxy)benzaldehyde is prepared by reacting p-hydroxibezaldehyde with 1,2-dibromoethane, in dry acetone. The product is then reacted with ethyleneglycol in toluene, with para toluene sulfonic acid as a catalyst, in dry conditions, in order to afford protection to the labile aldehyde groups. The protected 2-(4-(2-bromoethoxy)phenyl)-1,3-dioxolane is then reacted with potassium phthalimide, to afford 2-(4-(1,3-dioxolan-2-yl)phenoxy)ethanamine which is next coupled to the alginate using carbodiimide chemistry (using EDAC and NHSS as activators for alginate), as described previously. Then, the protecting group on the 1,3-dioxolane is removed by PPTS, in ethanol, and the free aldehyde is obtained. Any ligand protein may now be coupled by creating a Schiff base bond between the activated alginate and the amino group of the protein.

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