Clemmensen

Reduction of the aldehyde or ketone carbonyl group into methylene group with Zn amalgam.

Marthin modification - in boiling toluene with a yield of up to 90%.

Also see Kizhner-Wolff, Wolform-Karabinos and Schwenk-Papa.

Bibliography

• Clemmensen E., Ber., 1913, 46, 1837.
• Staschewski D., Angew. Chem., 1959, 71, 726.
• Nakabayashi T., J. Am. Chem. Soc., 1960, 82, 3900, 3906, 3909.
• Schmitt J. e.a., Bull. Chem. Soc., 1961, 340.
• Risinger G. E., Thompson J. A., J. Appl. Chem., 1963, 13, 346.
• Woodgate P. D., Quart. Rev., 1969, 23, 522.