[chuckyseagal]

i dont know where to start

[sjb]

For those of you playing along at home, here's the structure.

How about disconnection of the phenol to give the alkyl chain and something like 2'-hydroxydihydrochalcone as a first move back to starting materials?

It's unclear from my search whether Propafenone is the racemate or not, this may affect later moves.

S

[chuckyseagal]

well my first step was disconecting at the carboxyl group giving me a benzene and using acylation to get back

[sjb]

See, that's half the fun of retrosynthesis, there's often more than one way to answer the question.

Nothing wrong with what you're suggesting.

Let's run with what you have.

Now, how will you make the phenethylcarbonyl part of the molecule?

Or how do you propose getting the 1,2,3 substituted chain?

[chuckyseagal]

heres an update to what i have so far
http://www.putfile.com/pic/8034994

[sjb]

OK, I'm happy with what you've got up to the fluoride deprotection of the TMS group (though in practice you may want a bulkier protecting group as TMS is fairly acid sensitive, but not too bulky as you don't want to direct away from the ortho position for your acylation). This compound (the phenol), is what I have called "2'-hydroxydihydrochalcone" before, sorry if it confused you.

Anyway, for the next step, I would look into a compound called epichlorohydrin (http://en.wikipedia.org/w/index.php?title=Epichlorohydrin&oldid=198651023). Would this help?