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The impact of CaO on oakwood pyrolysis was explored by the Py-GC/MS at 500 °C. Ca(OH)2 presents on the CaO surface, indicating its partial hydration (noted as CaOOH). CaOOH promoted the ketonisation of carboxylic acids to aliphatic ketones, furfural to cyclopentanone/2-cyclopentenone, facilitated the elimination of the methoxy-phenolic compounds. The catalyst loading did not show any significant effect on the formation of acetone, while a noticeable reduction in the phenolics was revealed. Increasing catalyst loading almost eliminated CO2, acids, furans, aldehydes, ether groups, whilst the fractions of alcohols, esters, sugars, and alkoxybenzene decreased noticeably. The use of partially hydrated CaOOH in the CFP can create conditions where by-products generated during the ketonisation and phenolics upgrading reactions (CO2, H2O, CO) interact through the adsorption enhance water-gas-shift reaction and through coking reactions with formation of H2 used for hydrogenation during multistep conversion of furfural to cyclopentanone in a vapour phase.