Wolff–Kishner Reduction (C=O → CH₂ using NH₂NH₂ / KOH / ethylene glycol (high T))

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C=O → CH₂ using NH₂NH₂ / KOH / ethylene glycol (high T)

What each symbol means

SymbolWhat it stands for
KOHStrong base — promotes decomposition of hydrazone with loss of N₂
NH₂NH₂Hydrazine — forms hydrazone intermediate
ethylene glycolHigh-boiling solvent (b.p. 197°C)

When to use this

Strongly basic conditions at high temperature. Substrate must be stable in base. Complementary to Clemmensen (acidic). Huang–Minlon modification uses ethylene glycol as solvent.