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A series of photoacylations of 1,4-naphthoquinone with various aldehydes was conducted under continuous-flow conditions using Pyrex-filtered UVB light. Acetone was employed as both a triplet photosensitizer and a convenient solvent, allowing all materials to remain in solution and to be easily removed afterward. The corresponding acylated 1,4-naphthohydroquinone photoproducts were obtained in acceptable to excellent yields (30–90%) with residence times of just 70 minutes. The photoacylation process was successfully coupled with in-line oxidation, through which acylated 1,4-naphthoquinones were obtained.