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Topic: Carvone and tartaric acid  (Read 2572 times)

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Offline rolnor

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Re: Carvone and tartaric acid
« Reply #15 on: January 26, 2021, 08:59:26 AM »
I think you would get 1,4-addition if you mix the ketone with amine.

Offline sharbeldam

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Re: Carvone and tartaric acid
« Reply #16 on: January 26, 2021, 11:58:01 AM »
Can someone just give me a reaction that I can do on carvone that once I react it with tartaric acid it gives two diastereomers? I’m so confused now
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Offline Babcock_Hall

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Re: Carvone and tartaric acid
« Reply #17 on: January 26, 2021, 12:27:28 PM »
Free tartaric acid might or might not work, but a diester might be better.  I would make the ketal, using the ketone group of carvone.  After separation, I would hydrolyze.

Offline rolnor

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Re: Carvone and tartaric acid
« Reply #18 on: January 26, 2021, 12:43:47 PM »
I also thought of a ketal, mayby its complicated when you have the isopropylene group, this group can also react with alcohols under acidic conditions. I think you can do this without acid if you make a stannane of the tartaric ester. Then the question is, will these two diastereomeres separate in a good way? Maybe by crystallisation its possible to separate them, on silica-gel its less likely.

Offline sharbeldam

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Re: Carvone and tartaric acid
« Reply #19 on: January 26, 2021, 02:22:49 PM »
By saying ketal do you guys mean adding a diol or using the diol of the tartaric acid? Cause according to the book a modification need to happen on the carvone before reacting with the tartaric acid.
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Offline rolnor

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Re: Carvone and tartaric acid
« Reply #20 on: January 26, 2021, 02:25:21 PM »
Then its probably wrong to make a ketal.

Offline rolnor

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Re: Carvone and tartaric acid
« Reply #21 on: January 26, 2021, 02:33:03 PM »
You can reduce carvone to the alcohol and make a tartaric ester, separate, hydrolyze and oxidize. Not very easy though.
In this link you can se the reduction;

Edit; This is a bad idea, the two enatiomeres of carvone will create twoo different alcohols.

https://en.wikipedia.org/wiki/Carvone
« Last Edit: January 26, 2021, 03:10:24 PM by rolnor »

Offline rolnor

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Re: Carvone and tartaric acid
« Reply #22 on: January 26, 2021, 03:30:08 PM »
Maybe a enamine is the only way. The methyl group might hinder 1,4-addition.

Offline Babcock_Hall

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Re: Carvone and tartaric acid
« Reply #23 on: January 26, 2021, 03:59:21 PM »
By saying ketal do you guys mean adding a diol or using the diol of the tartaric acid? Cause according to the book a modification need to happen on the carvone before reacting with the tartaric acid.
Do I understand correctly that the book does not specify the modification?  Can you quote what they say?

Offline sharbeldam

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Re: Carvone and tartaric acid
« Reply #24 on: January 26, 2021, 04:17:46 PM »
Rolnor thank you!
Babock, i would have put the source but it is not in english, it just says there is a modification reaction (not specified) and then after it is modified it reacts with tartaric acid to produce 2 diastereoisomers that can be separated, perhaps what rolnor said is what they mean.

you guys all helped me a lot!
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Offline sjb

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Re: Carvone and tartaric acid
« Reply #25 on: January 26, 2021, 04:55:08 PM »
It may not even be a bond formation. but just cocrystallisation of carvone and the enantiopure acid

Offline rolnor

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Re: Carvone and tartaric acid
« Reply #26 on: January 27, 2021, 03:22:59 AM »
Sharbeldam says it should be some kind of change in the carvone molecule.

Offline AWK

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Re: Carvone and tartaric acid
« Reply #27 on: January 27, 2021, 07:02:49 AM »
Rolnor thank you!
Babock, i would have put the source but it is not in english, it just says there is a modification reaction (not specified) and then after it is modified it reacts with tartaric acid to produce 2 diastereoisomers that can be separated, perhaps what rolnor said is what they mean.

you guys all helped me a lot!
This is very important information that had to be provided at the very beginning. Due to the lack of this information, a few people wasted their time unnecessarily. You've been using this forum long enough to put your questions right!
AWK

Offline sharbeldam

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Re: Carvone and tartaric acid
« Reply #28 on: January 27, 2021, 06:09:03 PM »
Sorry I wasn't clear in my original post, the only reason for that was that the book mentioned it's a very known method, so I believed that and thought people would just know what I'm talking about. I did imply in the first page that I needed to make something from carvone to react it with the acid, but either way I apologize AWK and thanks!
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