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Topic: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?  (Read 9545 times)

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Offline SeriouSyrius

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Re: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?
« Reply #15 on: January 06, 2014, 08:25:41 AM »
That is the aldol reaction. This is a standard method for the preparation of such compounds. Analogues of curcumin, an interesting compound for various pharmacological applications, cancer for example.

Alright. Thanks! Helped a lot.  :) :) :)

Offline kriggy

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Re: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?
« Reply #16 on: January 07, 2014, 11:40:36 AM »
In the last attempt I belive you missdrew one hydroxy goup in your product. Shouldnt it be in para position instead of meta?

Offline SeriouSyrius

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Re: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?
« Reply #17 on: January 11, 2014, 08:28:27 AM »
Apparently the method I used isn't really good. I need to come up with a better one. I was thinking about this.







As for the picture below, I was asked to think about the 3 side products but after reading the notes I had about aldol reaction, I can't seem to find the side products. All I can think of is the mixed aldol reaction but the problem now is there are 0 alpha-hydrogen in 4-hydroxybenzaldehyde and 4 alpha-hydrogen in cyclohexanone. How does the mixed aldol reaction work when 4-hydroxybenzaldehyde have 0 alpha-hydrogen???


Offline discodermolide

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Re: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?
« Reply #18 on: January 11, 2014, 08:52:17 AM »
The mixed aldol reaction is possible with cyclohexanone.
You take the product from the aldol of cyclohexanone and the benzaldehyde and react it with cyclohexanone. See if you can come up with the other possibilities.

I'm sorry but your new scheme is worse than the one you gave in. The acid chloride of formic acid, I'm not sure it exists. Try and find a route by making a benzoate from benzene.
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Offline SeriouSyrius

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Re: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?
« Reply #19 on: January 11, 2014, 09:52:11 AM »
The final product of the aldol of Cyclohexanone and 4-hydroxybenaldehyde doesn't have any alpha-carbon also. Unless I bond it to only 1 side of cyclohexanone. Can I do that?




Incorrect character found

Offline discodermolide

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Re: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?
« Reply #20 on: January 11, 2014, 10:14:47 AM »
This compound is a possible intermediate:
O=C1CCCC/C1=C\C2=CC=C(O)C=C2

and can undergo an aldol with the aldehyde or cyclohexanone.
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Offline SeriouSyrius

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Re: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?
« Reply #21 on: January 11, 2014, 11:03:08 AM »
Oh so this is one of the side product? Sorry, need you to tilt your head to the left. :P




What about the previous picture I send? The side product I written there.

Offline discodermolide

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Re: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?
« Reply #22 on: January 11, 2014, 11:12:23 AM »
Yes that is also a possible side product.
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Offline SeriouSyrius

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Re: How to obtain (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone?
« Reply #23 on: January 11, 2014, 11:23:00 AM »
Alright I got understand the method but I can't seem to form the 3rd product. Unless this can be the product?




If that is not one of it, how about I switch the 2 side around but I don't think it make a difference? :/




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