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BIRCH REDUCTION
-By Khushi and Kulsoom
Introduction :
 The reduction of aromatic rings by means of alkali metals (such
as Na , K , Li ) in the liquid ammonia in the presence of
alcohol(ethanol) to give unconjugated dienes is called as Birch
reduction .
 Arthur J Birch , an Austrian chemist nailed down the structure
of the product in 1944 as a 1,4-cyclohexadiene derivatives .
 Liquid ammonia serves as a solvent .
 Alkali metals serves as electron donors .
 Alcohol acts as a proton donor.
 Occurs at temperature range : -80ºC to -33ºC
 It is regiospecific when substituents are attached .
Mechanism :
Application:
 Widely used in synthetic organic chemistry .
 Regiospecificity of the reaction is used to prepare various di-ene
derivatives .
When Electron Donating groups (EDG) are attached
(-OH, -OR , -CHO , -COOR )
 EDG remains on the unreduced (sp2) carbon atom ; thus the
ortho or meta carbons are reduced .
Eg . The reduction of Anisole :
When Electron Withdrawing groups (EWG) are attached
(-CONH2 , -COOH )
 EWG remains on the reduced (sp3) carbon atom ; thus the ipso
and para carbons are reduced .
Eg. Reduction of Benzoic acid
BIRCH REDUCTION_Mechanism and Applications

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BIRCH REDUCTION_Mechanism and Applications

  • 2. Introduction :  The reduction of aromatic rings by means of alkali metals (such as Na , K , Li ) in the liquid ammonia in the presence of alcohol(ethanol) to give unconjugated dienes is called as Birch reduction .  Arthur J Birch , an Austrian chemist nailed down the structure of the product in 1944 as a 1,4-cyclohexadiene derivatives .  Liquid ammonia serves as a solvent .  Alkali metals serves as electron donors .  Alcohol acts as a proton donor.  Occurs at temperature range : -80ºC to -33ºC  It is regiospecific when substituents are attached .
  • 4. Application:  Widely used in synthetic organic chemistry .  Regiospecificity of the reaction is used to prepare various di-ene derivatives . When Electron Donating groups (EDG) are attached (-OH, -OR , -CHO , -COOR )  EDG remains on the unreduced (sp2) carbon atom ; thus the ortho or meta carbons are reduced .
  • 5. Eg . The reduction of Anisole : When Electron Withdrawing groups (EWG) are attached (-CONH2 , -COOH )  EWG remains on the reduced (sp3) carbon atom ; thus the ipso and para carbons are reduced .
  • 6. Eg. Reduction of Benzoic acid