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Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone.In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate:
Reductive amination acetophenone ammonia Additionally, many systems catalyze reductive aminations with hydrogenation catalysts. [ 15 ] Generally, catalysis is preferred to stoichiometric reactions as they may improve reaction efficiency and atom economy, and produce less waste. [ 16 ]
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).
The term stems from cumene (isopropyl benzene), the intermediate material during the process. It was invented by R. Ūdris and P. Sergeyev in 1942 (USSR), [1] and independently by Heinrich Hock in 1944. [2] [3] This process converts two relatively cheap starting materials, benzene and propylene, into two more valuable ones, phenol and acetone.
Transfer hydrogenation to ketones leads to alcohols (the Meerwein-Ponndorf-Verley reduction), and in the presence of a chiral transition metal catalyst, this process may be rendered enantioselective. In the presence of a chiral diamine, ruthenium catalyzes the enantioselective transfer hydrogenation of aryl ketones with isopropanol. [11]
The Dakin oxidation. The Dakin oxidation (or Dakin reaction) is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide (H 2 O 2) in base to form a benzenediol and a carboxylate.
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Asymmetric hydrogenation of acetophenone by Noyori catalysts proceeds quantitatively ... and is an important step in the PO/SM process for the production of styrene. [10]