[SeriouSyrius]

Reference on compound: http://www.chemspider.com/Chemical-Structure.1468601.html

I was using benzene to convert it to 4-hydroxybenaldehyde and then I used cyclohexane to convert it to Cyclohexanone.

1 mole of Cyclohexanone + 2 moles of 4-hydroxybenaldehyde  ---NaOH(aq)--->  (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone

Is this right?

[discodermolide]

I would be more interested to see how you went from benzene to 4-hydroxy-benzaldehyde!
The latter compound is commercially available.

[SeriouSyrius]

[discodermolide]

The last reaction to make the phenol, how do you see this proceeding?
You have an aromatic aldehyde in the presence of conc. NaOH at high temperature, what other reaction could occur here?

[Altered State]

I'd rather go for a diazonium salt hydrolyisis, check Sandmeyer reaction.

[SeriouSyrius]

The last reaction to make the phenol, how do you see this proceeding?
You have an aromatic aldehyde in the presence of conc. NaOH at high temperature, what other reaction could occur here?

I got the last reaction from my notes. It says "Sodium Phenoxide + HCl(H+)---->Phenol"

As for the aromatic aldehyde with NaOH I think Aldol Reaction will occur? So I guess this part is wrong.


How about this method? I think i used diazonium salt to get OH.

[discodermolide]

I meant the substitution of Cl with OH.
How do you think this proceeds?
Aromatic aldehydes undergo a named reaction in the presence of strong base, can you think of it? Named after a famous Italian chemist from the 1800s.

[SeriouSyrius]

I meant the substitution of Cl with OH.
How do you think this proceeds?
Aromatic aldehydes undergo a named reaction in the presence of strong base, can you think of it? Named after a famous Italian chemist from the 1800s.

I don't really get what you mean. All i know is the substitution of Cl with OH is to get alcohol and so I can reduce the primary alcohol to aldehyde. For the reaction name, I got no idea. All I can think of is Aldol Reaction.

[discodermolide]

The reaction I am talking about is the Cannizzaro reaction of aromatic aldehydes to give the benzyl alcohol and the benzoic acid. http://en.wikipedia.org/wiki/Cannizzaro_reaction

I was just wondering if you knew how the substitution of Cl for OH worked (the reaction mechanism).

[SeriouSyrius]

The reaction I am talking about is the Cannizzaro reaction of aromatic aldehydes to give the benzyl alcohol and the benzoic acid. http://en.wikipedia.org/wiki/Cannizzaro_reaction

I was just wondering if you knew how the substitution of Cl for OH worked (the reaction mechanism).

Oh. I didn't hear before Cannzizzaro reaction. I'm still studying for Organic Chemistry. Currently studying about Benzene, Phenol, Aniline and Aldol Condensation. So how was my method of getting (2E, 6E)-2,6-bis(4-hydroxybenzylidene) cyclohexanone? It's a really important assignment and I need to try to get much information about it as I can. This is my overall method:

[discodermolide]

The new method certainly avoids problems with the Cannizzaro reaction. Using the diazonium salt is better.

The mechanism I was talking about, Cl going to OH (the original you showed) may go as I suggest in the attachment.
However I believe I am a bit ahead of your classes, sorry for any confusion I have caused. Anyway you have learnt a new reaction for yourself, and that's good.

[SeriouSyrius]

The new method certainly avoids problems with the Cannizzaro reaction. Using the diazonium salt is better.

The mechanism I was talking about, Cl going to OH (the original you showed) may go as I suggest in the attachment.
However I believe I am a bit ahead of your classes, sorry for any confusion I have caused. Anyway you have learnt a new reaction for yourself, and that's good.

It's alright. So if I'm not wrong the first overall method is alright but it's just that I have to use the method you attached? And the second method is also right?

[discodermolide]

I would go for the diazonium salt method. It is longer but avoids the side reaction I mentioned (Cannizzaro).

[SeriouSyrius]

Last question, about the combining of cyclohexanone with 4-hydroxybenaldehyde is there such reaction and is water the only side product? I found the reaction online so i'm wondering if it can be trusted.

[discodermolide]

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.