Work from this
Could you do standard selenate -> selenoxide and elimination chemistry on this, I fear it may open up the lactone.
It is hard to help you because we don't know what reactions you can use. I think your assignment being limited to book reactions is dumb
but what can you do.
Well, if we can sneakily add a "... and magazines ..." (sic
- i.e. journals, maybe that'll help)
Davy0488, what book are you using? If the exact reactions need to be in your book, does that faint alarm bell ringing in my head suggest that the actual synthesis is there too?
Nitriles are commonly introduced through the Sandmeyer reaction diazotonation of aniline and displacement with CN.
True, also dehydration of primary amides is another reasonably common "book example" in my experience.
Heh, nice find Agrobert. What about the double bond that they need?
I was actually thinking about this one and then a radical chloronation to the position next to the ester O. Then FC the benzene? The only thing I don't know is if the chloro group will end up there, or the double bond resonate to the other position.
I'm not sure, I think both isomers are fairly stable and not 100% certain of the energy barrier between the two. Certainly Joule and Mills (4th, page 307) suggest alpha and beta angelica lactone interconvert via 2-hydroxy-5-methylfuran, if I'm reading the page right.