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Topic: Retrosynthetic  (Read 4356 times)

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Offline Super Newb

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Retrosynthetic
« on: August 28, 2012, 07:04:40 PM »
Any help will be appreciate :)


Offline discodermolide

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Re: Retrosynthetic
« Reply #1 on: August 28, 2012, 09:31:31 PM »
Any help will be appreciate :)



So you are looking to synthesise methyl vinyl ketone?
The question mark after the down arrow should be the Aldrich catalogue. You buy it.
But if you want to make it it is made by and aldol reaction of acetone with formaldehyde followed by dehydration.
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Offline orgopete

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Re: Retrosynthetic
« Reply #2 on: August 29, 2012, 02:42:49 AM »
So you are looking to synthesise methyl vinyl ketone?


But if you want to make it it is made by and aldol reaction of acetone with formaldehyde followed by dehydration.

No, it's made by a Mannich reaction. It is an org syn prep, look it up.
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Offline discodermolide

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Re: Retrosynthetic
« Reply #3 on: August 29, 2012, 02:59:51 AM »
So you are looking to synthesise methyl vinyl ketone?


But if you want to make it it is made by and aldol reaction of acetone with formaldehyde followed by dehydration.

No, it's made by a Mannich reaction. It is an org syn prep, look it up.

Industrially, I thought it was done the way I posted!
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Offline mamid

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Re: Retrosynthetic
« Reply #4 on: August 29, 2012, 08:44:49 AM »
Quote
No, it's made by a Mannich reaction. It is an org syn prep, look it up.

Doesn't Mannich involve an amine?

Offline discodermolide

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Re: Retrosynthetic
« Reply #5 on: August 29, 2012, 09:04:43 AM »
So you are looking to synthesise methyl vinyl ketone?


But if you want to make it it is made by and aldol reaction of acetone with formaldehyde followed by dehydration.

No, it's made by a Mannich reaction. It is an org syn prep, look it up.

Well I searched Org. Syn. for Mannich reaction got 14 hits none involved prep of methyl vinyl ketone.
Searched for "synthesis of methyl vinyl ketone" 21 hits none involving Mannich reaction.
Have you got the link for the reference you gave, please?
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Offline orgopete

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Re: Retrosynthetic
« Reply #6 on: August 29, 2012, 09:38:20 AM »
I was wrong. I did this so long ago and I didn't bother to look it up that I was simply wrong.

I think this is what I remembered:
Arguably the best lab preparation for synthesizing methyl vinyl ketone is use of the Mannich reaction akin to the industrial process, using a dialkylamine hydrochloride to produce a beta-amino salt that can eliminate during heating to create the final MVK molecule.
http://www.monomerpolymer.com/index.php?option=com_content&view=article&id=14:mvk-information&catid=3:news&Itemid=115

The Mannich reaction is the org syn prep, http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0281
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Offline discodermolide

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Re: Retrosynthetic
« Reply #7 on: August 29, 2012, 09:43:35 AM »
I was wrong. I did this so long ago and I didn't bother to look it up that I was simply wrong.

I think this is what I remembered:
Arguably the best lab preparation for synthesizing methyl vinyl ketone is use of the Mannich reaction akin to the industrial process, using a dialkylamine hydrochloride to produce a beta-amino salt that can eliminate during heating to create the final MVK molecule.
http://www.monomerpolymer.com/index.php?option=com_content&view=article&id=14:mvk-information&catid=3:news&Itemid=115

The Mannich reaction is the org syn prep, http://www.orgsyn.org/orgsyn/prep.asp?prep=cv4p0281


Thank you.
By the way how was the ACS meeting, did it go well for you?
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