Birch reduction

Birch reduction
Named after Arthur Birch
Reaction type Organic redox reaction
Identifiers
Organic Chemistry Portal birch-reduction
RSC ontology ID RXNO:0000042

The Birch reduction is an organic reaction that is used to convert arenes to 1,4-cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent (traditionally liquid ammonia) with an alkali metal (traditionally sodium) and a proton source (traditionally an alcohol). Unlike catalytic hydrogenation, Birch reduction does not reduce the aromatic ring all the way to a cyclohexane.

The Birch reduction
The Birch reduction

An example is the reduction of naphthalene in ammonia and ethanol:

naphthalene Birch Reduction
naphthalene Birch Reduction