Nitric Acid → Acetophenone

HRID 2398188Notes

Reaction equation

HRID 2398188 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.S(=O)(=O)(O)O.[N+]([O-])(O)=O>[Ni].C(O)C>[C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:4][CH:5]=1)(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 8494m-Nitroacetophenone3×

Product 1

HCID 7410Acetophenone

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

With the nickel catalyst, if very pure m-nitroacetophenone is used (i.e., 100% by GLC as obtained, for example, by crystallization from ethanol) the hydrogenation will not occur or will occur slowly. Where crude (less than 100% purity) m-nitroacetophenone is used-the impurities present being acidic sulfuric acid, nitric acid, or other acid material contained in the m-nitroacetophenone as obtained directly from the nitration of acetophenone without further purification-the process is operable. Crude m-nitroacetophenone when suspended in water gives a strongly acid system with a pH of 2.6 to 3.2. If very pure m-nitroacetophenone is used and fails to hydrogenate, the addition of a few drops of sulfuric acid to the aqueous suspension will permit hydrogenation to occur to yield the desired product.

Sources & evidence

ORD record
ord-0c9e7f0bde1f4f6d95849850c87372e5
Source dataset
uspto-grants-1977_05
Patent number
US04024187

Reaction notes

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