Current continuous flow reactor (CFR) development and optimization primarily involves the investigation of process parameters such as flow and temperature to optimize a reaction. The advantages of CFRs for stable production -- including improved heat transfer, reproducible results, safety and cost considerations, and others -- generally result in comparable or improved yield compared to batch chemistry. However, the translation of a reaction from batch to continuous flow may be significantly improved following the thorough investigation of a batch reaction with analytical instrumentation.;In this work, the Swern oxidation of S-1-phenylethanol is optimized for continuous flow production via the combination of information discovered in batch and continuous flow validation methods. A model chemistry is investigated with Raman spectroscopy and chemometric modeling in continuous flow, demonstrating the capability of real-time monitoring conversion in a CFR. The Swern oxidation is investigated in batch using Raman spectroscopy, high performance liquid chromatography (HPLC), and gas chromatography tandem mass spectrometry (GC-MS), yielding new information about intermediate kinetics, product formation, and side-product decomposition pathways. A technique for rapidly determining steady state in a CFR is described, using the Swern oxidation as a model chemistry. Finally, the Swern oxidation of S-1-phenylethanol is optimized in a CFR using real-time quantitative Raman monitoring and the mechanistic information uncovered in the batch investigation. This improved CFR development and optimization pathway -- a thorough investigation of batch, coupled with optimization of a reaction through understanding of a chemistry -- offers significant advantages over the current paradigm, and is applicable to most CFRs. |