This may be Bayer-Villager variant, but Ive been away from teaching for awhile, and never used this reaction in my lab work, so it is not familiar to me. My intuition tells me chromic acid is not strong enough, but Id never bet my intuition against a good literature search.More
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From a SciFinder search, there are ~10 examples of oxidations of aryl methyl ketones resulting in a carboxylic acid using a chromium based reagent (usually dichromate but also chromium trioxide). This suggests the reaction is at least possible, although I think including it in a textbook is unwarranted.
One reaction slipped through my search that is informative (below). Notice that in the presence of a benzylic position that does contain a hydrogen, the methyl ketone is unchanged, while the other group is oxidized.
Taken together, it seems that chromium oxidation of an acetophenone to a carboxylic acid is slower than alkyl benzylic oxidation.
From a SciFinder search, there are ~10 examples of oxidations of aryl methyl ketones resulting in a carboxylic acid using a chromium based reagent (usually dichromate but also chromium trioxide). This suggests the reaction is at least possible, although I think including it in a textbook is unwarranted.
One reaction slipped through my search that is informative (below). Notice that in the presence of a benzylic position that does contain a hydrogen, the methyl ketone is unchanged, while the other group is oxidized.
Taken together, it seems that chromium oxidation of an acetophenone to a carboxylic acid is slower than alkyl benzylic oxidation.
I'd like to clear up one issue that has not been addressed in comments, but provides a weak answer.
There are NO benzylic hydrogens in acetophenone. So it is not possible based on what the textbook tells you.
I'd like to clear up one issue that has not been addressed in comments, but provides a weak answer.
There are NO benzylic hydrogens in acetophenone. So it is not possible based on what the textbook tells you.
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From a SciFinder search, there are ~10 examples of oxidations of aryl methyl ketones resulting in a carboxylic acid using a chromium based reagent (usually dichromate but also chromium trioxide). This suggests the reaction is at least possible, although I think including it in a textbook is unwarranted.
One reaction slipped through my search that is informative (below). Notice that in the presence of a benzylic position that does contain a hydrogen, the methyl ketone is unchanged, while the other group is oxidized.
Taken together, it seems that chromium oxidation of an acetophenone to a carboxylic acid is slower than alkyl benzylic oxidation.
From a SciFinder search, there are ~10 examples of oxidations of aryl methyl ketones resulting in a carboxylic acid using a chromium based reagent (usually dichromate but also chromium trioxide). This suggests the reaction is at least possible, although I think including it in a textbook is unwarranted.
One reaction slipped through my search that is informative (below). Notice that in the presence of a benzylic position that does contain a hydrogen, the methyl ketone is unchanged, while the other group is oxidized.
Taken together, it seems that chromium oxidation of an acetophenone to a carboxylic acid is slower than alkyl benzylic oxidation.
More
VOTE