Towards the development of bio-based material, the design of monomers from different perspectives is needed, starting with the election of the main structure. Wood is a highly relevant bio-source, especially in Sweden, for many biobased compounds in the new generation of sustainable and greener monomers. In particular, vanillin, derived from technical lignin, since is carry many different functionalities including aldehydes and phenols. Their distribution in the aromatic ring in para positions create two separate points that allow an enormous number of transformations to a monomer.Considering the economical aspect of bio-based materials, circularity is one of the key aspects. The incorporation of acetal groups in monomer structures was considered to provide possibility of chemical recycling under acidic conditions, increasing the chance of the recovery of the starting monomer, at the same time works as a spacer. In addition, the modification of phenol with an allyl group can allow sequential thiol-ene polymerization step.Applying this strategy in the vanillin looking for atom efficiency, some troubles in terms of yield were found relating to the equilibrium features in the acetal formation and the acidity of the phenol group. With the goal of decipher the chemical behaviour of vanillin, a thorough study was developed studying the optimization of the synthetical path, the nature of the pKa of different substituent groups or the effect of the selected solvent in the mechanism. As result, a strategy was developed for the synthesis of highly functionalized vanillin monomers in sustainable conditions at almost quantitative yield.