The Vespiary

The Hive => Chemistry Discourse => Topic started by: Hansje on April 24, 2002, 11:16:00 AM

Title: styrene to phenylacetic?
Post by: Hansje on April 24, 2002, 11:16:00 AM
Late last night, not completely sober, I was pondering the possibility of forming the pseudonitrosite of plain styrene, decomposing it and reducing the resulting nitrostyrene to phenyl acetaldehyde and oxidising the latter to phenylacetic acid. This morning I miraculously remembered my musings of the night before. I tried, but couldn't find anything using TFSE, so it's probably a stupid idea. Before I look any further I'd like to know if it really is and, if so, why.
Anybody?
Hansje high in proteine and fibre!
Title: DUUUR !
Post by: Elementary on April 24, 2002, 11:31:00 AM

Post 258134 (missing)

(foxy2: "New preparation of phenylacetic acid", Chemistry Discourse)

Nobodys home
Title: wilgerodt
Post by: Aurelius on April 24, 2002, 10:13:00 PM
aurelius is just finishing up a styrene to phenylacetic acid with mass-spec analysis to boot.  so far, just have the sodium salt of the final product but a GOOD yeild seems to be in order.  haven't done any weighings of the salt so yeilds are still up in the air.  used the procedure at Rhodium's site

https://www.thevespiary.org/rhodium/Rhodium/chemistry/willgerodt.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/willgerodt.html)


with a couple of variations (very minor)  when completely done a write up will be posted. 

Over-all, aurelius can say this- stinky, but VERY EASY.
Title: wilgeroth
Post by: Hansje on April 25, 2002, 03:07:00 AM
Well, morpholine is out of the question for me and the S + NH4OH thing sounds pretty noxious. So my question, why not pseudonitrosite, remains unanswered.
Hansje high in proteine and fibre!
Title: Wha?
Post by: PrimoPyro on April 25, 2002, 05:02:00 AM
You think ammonia is more noxious than nitric oxide fumes? Oh man are you in for a surprise.
Vivent Longtemps La Ruche!
Title: Noxious
Post by: Rhodium on April 25, 2002, 05:07:00 AM
PP: It is not the ammonia, but the copious quantities of H2S generated in the Willgerodt reaction that is the "problem". I'd choose a pseudonitrosite reaction in my kitchen over a willgerodt in my garage any day of the week.
Title: nitric oxide
Post by: Hansje on April 26, 2002, 09:31:00 AM
I'd choose a pseudonitrosite reaction in my kitchen over a willgerodt in my garage any day of the week.

I wholeheartedly agree.

You think ammonia is more noxious than nitric oxide fumes? Oh man are you in for a surprise.

No, I don't think that and I won't be surprised by any fumes. I'll pass 'm over NaOH solution, which will readily absorb it to form NaNO2 again. Cleans up most noxiousness. Very economic too. :)
Hansje high in proteine and fibre!