The utilization of alcohols as alkylation surrogates for aldehydes represents a highly desirable reaction route in organic chemistry since alcohols can be directly obtained from biomass. Therefore, efficient catalytic procedures for in situ generation of carbonyl moieties, based on noble- and nonprecious transition metals were described in the last decades by a manifold of researchers, including reports from our group. However, it has been shown that benzyl alcohols can be swiftly oxidized to the corresponding carbonyls upon treatment with a strong base under atmospheric conditions. In fact, various condensation reactions can be carried out with benzyl alcohols in presence of a (catalytic amount of) base without transition-metal complexes. It was found that the majority of these transformations are driven by alkali metal catalyzed Meerwein-Ponndorf-Verley reduction/ Oppenauer oxidation (MPV-O) reactions. A similar transformation represents the synthesis of imines from benzyl alcohols and anilines -a reaction that has been known since the 1950s but seems to be largely overseen in the organometallic's community (Scheme 1). In contrast to transition metal catalyzed reactions, only little mechanistic insights are provided so far for this process. In this context, we propose a detailed reaction mechanism, based on experimental findings and extensive theoretical studies.