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Topic: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?  (Read 6948 times)

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Offline ss1234

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Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« on: October 24, 2016, 01:56:07 PM »
Does anyone know all of the steps to the synthesis please?

This is what I have so far is it on the right step?

1. Br2/FeBr3

2. methyl 1-cyclohexene carboxylate

3. Pd (Oac)2
« Last Edit: October 24, 2016, 03:01:39 PM by ss1234 »
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Offline Babcock_Hall

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #1 on: October 24, 2016, 02:38:59 PM »
It is a forum rule that you must show your attempt or thoughts before we can help you.  Have you learned any reactions that look similar?
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Offline AWK

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #2 on: October 24, 2016, 05:04:11 PM »
Heck reaction with cyclohexene gives mixture of products with low yield. Probably the same concerns cyclohexene derivatives.
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Offline Babcock_Hall

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #3 on: October 24, 2016, 05:11:41 PM »
I would have thought that the electron-withdrawing group causes a preference in the regiochemistry.
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Offline kriggy

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #4 on: October 25, 2016, 04:35:38 AM »
I think it might help if you draw the whole structure of the ester instead of just COOMe and then look at the positions of double bond and the ester.
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Offline rolnor

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #5 on: October 25, 2016, 07:05:28 AM »
The Heck-reaction does not remove the doublebond?
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Offline AWK

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #6 on: October 25, 2016, 09:07:03 AM »
Quote from: rolnor on October 25, 2016, 07:05:28 AM
The Heck-reaction does not remove the doublebond?
Reduction of double bond in the reaction product will not be a problem but add one step more.
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Offline rolnor

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #7 on: October 25, 2016, 09:21:42 AM »
Yes, the doublebond will be tetrasubstituted so it will need som pressure. I can not see the step i the list though?
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Offline orgopete

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #8 on: October 25, 2016, 06:08:30 PM »
Well, it looks like organometallic chemistry is being discussed in class. I agree with the basic methodology. Might another organometallic reagent work?
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Offline rolnor

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #9 on: October 26, 2016, 01:54:15 PM »
A cuprate would do the trick offcourse, that would give the saturated, desired product.
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Offline ss1234

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #10 on: October 27, 2016, 02:23:55 PM »
Quote from: ss1234 on October 24, 2016, 01:56:07 PM
Does anyone know all of the steps to the synthesis please?

This is what I have so far is it on the right step?

1. Br2/FeBr3

2. methyl 1-cyclohexene carboxylate

3. Pd (Oac)2, Et3N

4. H2/pd

Please confirm


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Offline rolnor

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #11 on: October 27, 2016, 03:45:29 PM »
Ok, I did not se the last step in the first list, the H2/PdC step.
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Offline ss1234

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #12 on: October 27, 2016, 04:33:31 PM »
Quote from: rolnor on October 27, 2016, 03:45:29 PM
Ok, I did not se the last step in the first list, the H2/PdC step.


Does it seem complete, do you think there are any mistakes? Thank you so much for your help
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Offline AWK

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #13 on: October 27, 2016, 04:54:16 PM »
As I told previously, with unsubstituted cyclohexene, many compounds are formed, vinylation and unconjugated products prevail. These main products do not contain your needed carbon skeleton.

I think that much better will be
1. Anti-Markovnikov HBr addition to cyclohexene
followed by
2. Friedel-Crafts alkylation of benzene.
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Offline rolnor

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Re: Synthesize reaction using Methyl 1-cyclohexenecarboxylate and benzene?
« Reply #14 on: October 28, 2016, 07:39:35 AM »
But there is a estergroup present, does not that give a better result with Heck?
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