Question

All the praise in the world to the person that can help me with this:
For a final project I have to synthesize the following molecule, http://www.pherobase.com/database/compound/compounds-detail-3,4-dihydro-8-hydroxy-3me5me7me-isocoumarin.php
how could this molecule be synthesized from chemicals that could be bought online?

Answer 1

wow!

Answer 2

I think you would start with phenol. and then conduct two friedal crafts alkylation reactions.

Answer 3

i'm not really sure if this is the best possible synthesis but you could probably start with phenol.

I'm wondering though. If we can conduct two friedal crafts alkylations where we use methyl chloride and the OH hydroxyl group would be ortho and para directing. the first group would go on para while the second one would go on ortho to the hydroxyl.



I think the big problem here is getting the other ringed structure on. this could be done VIA a dies aldler reaction.

I'm going to look for a much better way.

Answer 4

Thank you so much for helping us!! I have to go now but I'm going to look into it this afternoon

Answer 5

Okey so how do we know that in the friedal crafts alkylation the methyl groups will go in the right places? (so phenol wont turn into e.g. 2,5-methylphenol)
A Diels-Alder reaction is indeed a very good idea!!
I must say that I am not that great of a chemist (I didnt know either of these reactions yet), so I might ask some not-so-great questions.

Answer 6

Also, isn't it neccesairy in a diels-alder reaction to have a double bond where the 2 molecules will join (see drawing), but this isn't possible here right? since the oxygen can't normally bind to 3 other atoms?