Sciencemadness Discussion Board

Phenylacetic acid to ethylbenzene?

RebeccaOlson - 19-3-2017 at 06:36

Hi guys, is it possible to reduce phenylacetic acid to ethylbenzene? I know the double bonded oxygen can be removed with LiAlH, but I don't know how to remove the OH. Thank you <3



[Edited on 19-3-2017 by RebeccaOlson]

JJay - 19-3-2017 at 06:45

It's not trivial... you could reduce it to 2-phenylethyl alcohol with lithium aluminum hydride, dehydrate it with sulfuric acid to styrene, and reduce the styrene by catalytic hydrogenation, but none of these steps are particularly high-yielding, and you might as well just start with styrene.

RebeccaOlson - 19-3-2017 at 06:57

BABE! Thanks heaps :D

Db33 - 19-3-2017 at 07:11

why on earth would u do this? ethyl benzene is very easy to obtain, whereas PAA is very hard.

RebeccaOlson - 19-3-2017 at 07:15

Hahaha it's for theory, I didn't want to use benzoic acid and toluene because they might be affected by the ring. Would LiAlH, then chromyl chloride, then more LiAlH work too?

EDIT: That won't work :(

[Edited on 19-3-2017 by RebeccaOlson]

CuReUS - 19-3-2017 at 07:21

Quote: Originally posted by RebeccaOlson  
Hi guys, is it possible to reduce phenylacetic acid to ethylbenzene?

you could do it in 4 ways:-
1.using HI/red P-http://www.askiitians.com/forums/Organic-Chemistry/can-red-p...
2.using Et3SiH -http://chemistry.mdma.ch/hiveboard/serious/000194986.html
3.Convert it to ester then this-http://chemistry.mdma.ch/hiveboard/chemistrydiscourse/000433...
4.By electrochemistry
Quote:
I don't know how to remove the OH.

http://www.organic-chemistry.org/synthesis/C1H/deoxygenation...
Quote: Originally posted by RebeccaOlson  
Would LiAlH, then chromyl chloride, then more LiAlH work too?
EDIT: That won't work :(

It would if you used TCT/DMF instead of chromyl chloride -http://pubs.acs.org/doi/abs/10.1021/ol017168p


[Edited on 19-3-2017 by CuReUS]