Making Benzocaine: The Local Anesthetic That Changed Medicine

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Discover the science behind one of the first synthetic anesthetics benzocaine and how it helped change the face of modern medicine. In this video, we dive into the full multi-step organic synthesis of benzocaine from p-toluidine, showcasing the chemistry, the historical context, and the real lab work that makes it all possible.

We'll start with the acetylation of p-toluidine to form p-acetotoluidide, then oxidize that to p-acetamidobenzoic acid using potassium permanganate. After hydrolysis, we recover p-aminobenzoic acid (PABA), a valuable intermediate used in dyes, sunscreens, and pharmaceuticals. Finally, we esterify PABA to synthesize benzocaine—the local anesthetic that replaced cocaine in medical practice and helped launch an entire class of safer pain-blocking compounds.

Along the way, we’ll explain every step in plain terms, walk through reaction mechanisms, troubleshoot common issues, and run instrumental analysis (GC-MS ) to verify the product.

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References and uses:
Adams, R., Johnson, J. R., & Wilcox, C. F. (1979). Laboratory experiments in organic Chemistry. MacMillan Publishing Company. (297-298, 307-309)

Chapters:
00:00 Introduction
01:45 P-Acetotoluidide
04:37 P-Acetamidobenzoic Acid.
7:15 P-Aminobenzoic Acid (PABA
09:40 Benzocaine
11:57 Analysis

Thanks for watching!