Tylenol Synthesis

This synthesis is even easier than Advil, and it takes a mere three steps to complete. Let's get started:

Step 1: Begin with phenol; it's easy to acquire and super cheap. Dump it in some HNO3 and H2SO4, to add an NO2 group on the para position on the ring. Note: you're going to get some ortho substituents too, so you'll obviously have to separate them out.

Step 2: Reduce the NO2 to NH2 using H2, Pd/C.

Step 3: This step is clever... I didn't think of it at first. It's an acetic anhydride - really easy to acquire as well. The NH2 attacks because it's less electronegative (thus a better nucleophile) than the oxygen on the opposite side. My initial thought was to create an N2+ ion and displace it with a nitrogen salt such as NaNH-R. I think using acetic anhydride is classier, though.

Ta-da. Boom - Done.