In this paper, we present a concise and technique-heavy route to the synthesis of dimedone for a second-year organic chemistry curriculum. Our preparation of dimedone guides students through a Michael addition followed by a Dieckmann cyclization, basic ester hydrolysis, and thermal decarboxylation, while allowing time for mechanistic discussion and analysis of the product. The wide variety of techniques covered led this to be a pedagogically diverse experiment. This task is thoroughly tested and suitable for a 6 hour laboratory class (with a 1 hour lunch break) or two 3 hour stand-alone sessions.