Maybe just my bad luck then. Every time I seem to touch fuming nitric acid bad things happen. What sort of scale are you talking - are you chromatograhing, or recrystallising, or how?
We've done anywhere on the scale of a few grams up to 50g starting bromocompound. Then we chromatograph it, since effectively recrystallizing the ortho or para and not the other isomer was pretty unlikely. The chromatography is equally frustrating on a large scale if you don't use a large enough column. Additionally, since the spots are so close it uses an incredible amount of solvent. Last time, I chromatographed a large column and went through about 5L of Hexane and probably 100+ fractions.
Well, not just grignard, 2 equivalents of Li etc, I'm just using metallation as a generic term for that umpolung style disconnection
Ah ok.
Don't know how up-to-date the page is, whether it's any use chemically, or a price; but I found http://www.prosynth.com/exstock.php here in the UK who claim 600g of 4-Nitrocinnamyl alcohol (CAS RN 1504-63-8).
Yea, I found out the prices. Pretty decent, and the 4-nitrocinnamylaldehyde is comercially available
I'm not 100% sure on reducing the isolated alkene in the presence of the nitro-group - something like Wilkinson's Catalyst?
This was the hardest part to figure out, but I did find a very nice synthesis that I'm going to look into.
If you have the alcohol maybe then tosylate it to activate it to displacement or similar. Have you even tried direct displacement of the halide with the amine. I seem to recall a prep using something like wet dioxane and inorganic base to avoid the over substitution viz. RNH2 -> RN(R')2. Can try and find it if you want.
If you could find a reference for that, that would be great, I'd appreciate it. More options are better.
I don't have the reference in front of me, but I'll post when I do. It selectively reduces the double bond in the cinnamylaldehyde with 94% yield and very mild conditions.
Thanks again for the thoughts, greatly appreciated!
Additionally, are you aware of any protecting groups for a nitro group? If we could protect the nitro, we could use a more standard reduction of the double bond. My cursory search didn't turn up anything though.