Introduction. Eugenol, also known as 4-allylbenzene-1,2-diol, a metabolite present in Syzygium aromaticum essential oil used as an aromatic agent for foods, fragrances and in the dentistry area, has been the object of incessant research due to its antibacterial, antifungal, antiprotozoal, and anthelmintic activity. Thus, studies on eugenol, as scaffold for several structural modifications, with great interest in medicinal chemistry, have been described aiming the continuous need for new and potent compounds with application in therapy. Aim. The approach used in this work illustrates procedures for the synthesis of eugenol derivatives aiming the preparation of novel compounds through easy and simple chemical reactions. Methods. Synthesis of 5-(2,3-dibromopropyl)-2-methoxyphenol (1). To a 50 mL flask containing 50 mg eugenol (0.3 mmol), in 4 mL glacial acetic acid, under stirring was added 15 μL of bromine (0.3 mmol), in drops, with this system being coupled to a condenser. Then 19 mg of sodium carbonate (0.18 mmol) were added observing CO2 release during the addition. The reaction mixture presented a viscous and transparent appearance. The reaction mixture was then heated at 80°C for 1 hour. Finally, the mixture was concentrated on the rotary evaporator and ethyl acetate was added and water/ethyl acetate extraction was performed (3 x 10 ml). Preparation of O-derivatives through Williamson synthesis. To a solution containing Eugenol (1 g, 6.1 mmol), in acetone (5 mL), under stirring was added potassium carbonate (1.7 g, 12.2 mmol). After 20 min, 0.66 mL of iodoacetonitrile (9.15 mmol) was added to the resulting solution and the stirring was continued at room temperature for 3h. Finally, a chromatographic column was performed using a hexane/ether (10:1) as eluent and pure compounds 3 and 4 were obtained. Eugenol-naphtoquinone conjugate 2 was prepared in similar method as 3 and 4. Results. Eugenol derivatives were prepared by Williamson synthesis and electrophilic addition and elucidated by 1D/2D NMR spectroscopic analysis. Conclusion. Eugenol was presented as an interesting building block in towards to different pathways for derivatives preparation. Therefore, future and continuous investigations on eugenol structure modifications is worth.