In Gallagher-Hollander Degradation (1946) pyruvic acid is detached from a linear aliphatic carboxylic acid giving a new acid with 2 carbon atoms less. The original reaction concerns the conversion of bile acid in a sequence of reactions: acid chloride (2) formation by thionyl chloride, diazoketone formation (3) by diazomethane, chloromethyl ketone formation (4) by hydrochloric acid, organic reduction of chlorine into methylketone (5), ketone halogenation into 6, elimination reaction with pyridine to enone 7 and ultimately oxidation with chromium trioxide to bisnorcholanic acid 8.
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