Sturge11
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MgBr2 Cell for Selective Oxidation Sec. Alc. to Ketone
Hello Team,
Anyone have any experience oxidizing a secondary alcohol to a ketone with and electrochemical cell? I have a paper on this oxidation happening with
98% yield. Paper detailed enough to illustrate less desirable yields if substitutions are made. What do you think?
Source:
https://www.sciencedirect.com/science/article/pii/S277322312...
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Random
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I was researching something like this like 10-15 years ago.
I always seen as getting Ketone into Alcohol as much more harder than going from Alcohol into Ketone.
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Sturge11
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Quote: Originally posted by Random  | I was researching something like this like 10-15 years ago.
I always seen as getting Ketone into Alcohol as much more harder than going from Alcohol into Ketone. |
This is only half good in my case - because I am wanting a two-step here. I am wanting a 3b alcohol oxidized to ketone before oxidizing a ketone into
an alcohol. Your findings seem odd to me - just because of the complexity surrounding taking an alcohol and oxidizing it into a ketone and the dozens
of steps that happen very fast.
Either way - if I can get the first portion done, where I get the ketone, reduce with NaHB4.
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Random
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| Quote: Originally posted by Sturge11 | | Quote: Originally posted by Random | I was researching something like this like 10-15 years ago.
I always seen as getting Ketone into Alcohol as much more harder than going from Alcohol into Ketone. |
This is only half good in my case - because I am wanting a two-step here. I am wanting a 3b alcohol oxidized to ketone before oxidizing a ketone into
an alcohol. Your findings seem odd to me - just because of the complexity surrounding taking an alcohol and oxidizing it into a ketone and the dozens
of steps that happen very fast.
Either way - if I can get the first portion done, where I get the ketone, reduce with NaHB4. |
Depends what you mean by 3b alcohol and also I am not sure how you want to oxidize ketone into alcohol.
Dozens of steps that happen very fast would be like if you were to go from alcohol into oxidated derivate and you would want to catch an aldehyde.
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Sturge11
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| Quote: Originally posted by Random | | Quote: Originally posted by Sturge11 | | Quote: Originally posted by Random | I was researching something like this like 10-15 years ago.
I always seen as getting Ketone into Alcohol as much more harder than going from Alcohol into Ketone. |
This is only half good in my case - because I am wanting a two-step here. I am wanting a 3b alcohol oxidized to ketone before oxidizing a ketone into
an alcohol. Your findings seem odd to me - just because of the complexity surrounding taking an alcohol and oxidizing it into a ketone and the dozens
of steps that happen very fast.
Either way - if I can get the first portion done, where I get the ketone, reduce with NaHB4. |
Depends what you mean by 3b alcohol and also I am not sure how you want to oxidize ketone into alcohol.
Dozens of steps that happen very fast would be like if you were to go from alcohol into oxidated derivate and you would want to catch an aldehyde.
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on the 3rd Carbon in the beta position I have an OH functional group. The idea here is to oxidize the OH functional group through an electrochemical
cell using MgBr2. Should selectively oxidize the OH group resulting in the end-game of a ketone functional group =O. The process that this goes
through is beyond my understanding, but initially the oxidation lends itself to the hydroxyl becoming a carboxylic acid I think? I'm less worried
about the specific mechanism and more in just that my understanding is correct - I can oxidize my way from alcohol to ketone. Past that point, I can
vet for selectivity and have at it.
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bnull
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| Quote: Originally posted by Sturge11 | | The process that this goes through is beyond my understanding, but initially the oxidation lends itself to the hydroxyl becoming a carboxylic acid I
think? I'm less worried about the specific mechanism and more in just that my understanding is correct - I can oxidize my way from alcohol to ketone.
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There's no carboxylic acid intermediate.
But you're right about going from a sec alcohol to a ketone. Nice article.
Quod scripsi, scripsi.
B. N. Ull
P.S.: Did you know that we have a Library?
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