phenylacetic acid

[obituary]

Baeyer-Villiger Rearrangement of a ketone to an ester.
well, the ketone can be anything along the lines of 1-phenyl-hexamethylbadass-2-one

as long as the phenyl is 1-position and the alkyl group has a carbonyl at the 2-position
yes- so take something like 1-phenyl-hexan-2-one  and peracid it
you get the respective esters and the acids---- so hydrolyze to get the acids
basify and extract with water    obit'll use NaCO3 in case it's sensitive to strong acids
re-acidify and bam- phenylacetic acid

obit thinks that max yeild for our acid would be 50%   b/c it doesn't say which side the ester forms on the ketone- so if it splits 50/50 on either side- then 50% would be the max possible amount

just a thought

[obituary]

anybody?

[Rhodium]

Yes, the reaction should work all right in theory, but I don't know about if the reaction would be selective for cleaving on one side or another of the carbonyl. Do you have any suggestions about what cheapish ketone to start with? We wouldn't want to start with P2P, would we?

[obituary]

point is that the average P2something ketone isn't going to be watched and they can all be converted to P2P in theory.
and no, obit hasn't even approached working out the procedure.  wanted to run it by some others first. 
and if you're serious about the "start with P2P" question, then think about the cycle it would lock you into. 
the purpose is to create P2P from other ketones similar to it.

[Rhodium]

I wasn't serious when saying you could start with P2P, but seriously I don't know of any cheap phenyl-2-ketones you could start your synthesis with. If you know any, please enlighten me.

[obituary]

if obit finds some, will share. if not, then oh well.
what about oxidation of a 2-ol ?

[Rhodium]

That would also work, followed by a bayer-villiger oxidation.

[obituary]

yes, but are the 2-ol's cheap enough?  readily avail?  shoot even a halo compound, swap with base to give OH, and then oxidize.  but only if the materials are cheap and readily avail.

[Rhodium]

I would buy phenethylalcohol (it is not controlled), and oxidize its ass of to phenylacetic acid directly.

[obituary]

http://www.pmf.ukim.edu.mk/PMF/Chemistry/reactions/baeyer-villiger.htm