Sciencemadness Discussion Board

3-methyl-1-phenylbut-2-en-1-one

Eddygp - 10-9-2014 at 07:22

I thought about a synthesis of this compound starting with... POLYSTYRENE!!

First, you heat the poly(styrene) to form styrene, the monomer (in the presence of polymerisation inhibitors if necessary).
Secondly, the bromination of the pi bond would yield (1,2-dibromoethyl)benzene.
This is reacted with two equivalents of sodium amide, eliminating the bromine atoms and two hydrogen atoms, creating a triple bond.
Via the Favorsky reaction or the Meyer-Schuster rearrangement reacting it with propanone, this would yield the product: 3-methyl-1-phenylbut-2-en-1-one

Is this viable?
What can I do with the product? (any peculiar use?)
Should I just perform a SN2 reaction with the sodium phenylacetylide, having more interesting products?

Thanks, as always!

forgottenpassword - 10-9-2014 at 07:54

Quote: Originally posted by Eddygp  

What can I do with the product?

You've planned a synthesis to make a compound that you have no use for?

Eddygp - 10-9-2014 at 07:57

Quote: Originally posted by forgottenpassword  
Quote: Originally posted by Eddygp  

What can I do with the product?

You've planned a synthesis to make a compound that you have no use for?

I haven't planned it, I actually have just thought about it. I realised that I could synthesize phenylacetylene and I thought about what to do with it.

bbartlog - 10-9-2014 at 08:17

A member did this synthesis (or one almost identical; the final step apparently can be done with NaOH rather than sodium amide):

http://www.sciencemadness.org/talk/viewthread.php?tid=18681

(edit): except that you were proposing an additional final step. I have no idea about the feasibility of that.


[Edited on 10-9-2014 by bbartlog]

Eddygp - 10-9-2014 at 10:13

Quote: Originally posted by bbartlog  
A member did this synthesis (or one almost identical; the final step apparently can be done with NaOH rather than sodium amide):

http://www.sciencemadness.org/talk/viewthread.php?tid=18681

(edit): except that you were proposing an additional final step. I have no idea about the feasibility of that.


[Edited on 10-9-2014 by bbartlog]


In fact, I found a video in youtube just a couple of minutes ago, posted by some UC238, who I suspect was Unintentional Chaos. Of that synthesis.

Eddygp - 12-9-2014 at 06:44

When threads are moved to Beginnings, the post rate declines to almost zero. Hmm.

Mesa - 12-9-2014 at 12:29

The reason nobody is replying has nothing to do with the forum this thread is in. You are asking a question after giving only a vague outline of a synthesis route, without any references, and a target compound that nobody would have a use for anyways.

It's likely that anyone answering questions regarding feasability etc. would have had to search relevant literature for the information. Perhaps you could too?
At least then, you could post links to whatever you find and not worry about moderators moving your threads around anymore.