The use of lignocellulosic biomass to obtain biofuels and chemicals produces a large amount of lignin as a byproduct. Lignin valorization into chemicals needs efficient conversion processes to be developed. In this work, hydrocracking of organosolv lignin was performed by using nickel Raney catalyst. Organosolv lignin was obtained from the pretreatment of eucalyptus wood at 170 °C for 1 h by using 1/100/100 (w/v/v) ratio of biomass/oxalic acid solution (0.4% w/w)/1-butanol. The resulting organic phase of lignin in 1-butanol was used in hydrogenation tests. The conversion of lignin was carried out with a batch reactor equipped with a 0.3 L vessel with adjustable internal stirrer and heat control. The reactor was pressurized at 5 bar with hydrogen at room temperature, and then the temperature was raised to 250 °C and kept for 30 min. Operative conditions were optimized to achieve high conversion in monomers and to minimize the loss of solvent. At the best performance conditions, about 10 wt % of the lignin was solubilized into monomeric phenols. The need to find a trade-off between lignin conversion and solvent side reaction was highlighted.