Following the importance of the conversion of lignin compounds into beneficial products, a new cleaner production strategy is proposed. To this end, simulated lignin-derived syngas was utilized instead of pure hydrogen for anisole and cyclohexanone conversion over a platinum catalyst. The experiments at 300–400 °C and 1–15 bar are addressed. The impact of weight hourly space velocity (WHSV) is also investigated. The new strategy offers high activity, selectivity, and yield for the conversion of anisole and cyclohexanone to possibly value-added products. Anisole conversion results in the formation of phenol, cyclohexanone, and methylated phenols. Cyclohexanone reaction produces cyclohexane, cyclohexene, benzene, cresols, phenol, and toluene. Increasing reaction temperature and pressure enhances the conversion of the reactants while increasing WHSV decreases the conversion. The highest anisole (87.44%) and cyclohexanone (77.02%) conversions were obtained at 400 °C, 15 bar, and the smallest WHSV. Temperature, pressure, and WHSV had major effects on the conversions and product distributions. The highest hydrocarbon yields and carbon-to-oxygen ratio enhancement (C/O RE) were managed at different conditions for anisole and cyclohexanone. The present study indicates that the new syngas-assisted strategy could be utilized for the conversion of lignin-derived compounds to hydrocarbons and possibly value-added products.