Bouveault-Blanc reaction

from Wikipedia, the free encyclopedia

The Bouveault-Blanc reaction or Bouveault-Blanc reduction is a reaction from the field of organic chemistry . It was discovered in 1903 by the French chemists Louis Bouveault (1864-1909) and Gustave Louis Blanc (1872-1927) and named after them. This reaction is a reduction of esters to alcohols .

Overview reaction

It is the reduction of a Carbonsäureesters (R 1 COOR 2 ) to the corresponding primary alcohol (R 1 OH) with the aid of metallic sodium and alcohol - for example ethanol - instead:

Synthesis of alcohols from esters or fats; R 1 , R 2 = organic radicals.

The reaction is an inexpensive alternative to the reduction of esters to primary alcohols and is carried out in industry for reasons of cost instead of reductions with expensive lithium aluminum hydride .

Reaction mechanism

Metallic sodium is a reducing agent with one valence electron ; that is, it can only give off one electron . So it takes four sodium atoms to completely convert an ester to alcohol .

Reaction mechanism of the Bouveault-Blanc reduction; R 1 , R 2 = organic radicals; R 3 = ethyl radical.

This reaction is radical . The constant reaction with the metallic sodium and the ethanol produces a primary alcohol after several reaction steps . Ethanol acts as a proton donor . However, other alcohols are also suitable as proton donors.

See also

Individual evidence

  1. ↑ Merriam-Webster Dictionary: Bouveault-blanc reduction .
  2. ↑ Bouveault, Blanc, Compte Rendu Acad. Sci., Paris, Volume 136, 1903, pp. 1676-1678.
  3. ↑ Bouveault, Blanc, Bull. Soc. Chim., Vol. 31, 1904, pp. 666-672.
  4. ↑ a b c d Z. Wang (Ed.): Comprehensive Organic Name Reactions and Reagents, 3 Volume Set . John Wiley & Sons, Hoboken, New Jersey 2009, ISBN 978-0-471-70450-8 , p. 494.
  5. ↑ a b H. Krauch, W. Kunz: Name reactions of organic chemistry , Dr. Alfred Hüthig Verlag, Heidelberg 1961, p. 69.
  6. ↑ Z. Wang (Ed.): Comprehensive Organic Name Reactions and Reagents, 3 Volume Set . John Wiley & Sons, Hoboken, New Jersey 2009, ISBN 978-0-471-70450-8 , p. 493.