[zuriel]

Hi guys,

I'm wondering if anyone knows of any procedures/protocols for functionalizing either ring of 1-naphthylacetic acid (I do need the 2-position kept free) ?

I've tried having a look around on reaxys but can't seem to find anything. I feel like I must be doing the search wrong.

Any advice along the lines of :

-fomylations
-sulfonations
-nitrations

or other reactions would be greatly appreciated!

[sjb]

Hi guys,

I'm wondering if anyone knows of any procedures/protocols for functionalizing either ring of 1-naphthylacetic acid (I do need the 2-position kept free) ?

I've tried having a look around on reaxys but can't seem to find anything. I feel like I must be doing the search wrong.

Any advice along the lines of :

-fomylations
-sulfonations
-nitrations

or other reactions would be greatly appreciated!

I would imagine things wouldn't be appreciably different in terms of protocols for phenylacetic acid - any luck there? A quick web search yields e.g. J. Org. Chem., 1951, 16 (10), 1588–92

DOI: 10.1021/jo50004a015

[zuriel]

Thank you very much, that document is VERY helpful!!

[wildfyr]

Boiling it in sulfuric/nitric acid is pretty much guaranteed to nitrate it. The trick is how many times the ring gets nitrated

[zuriel]

That wouldn't really bother me too much I guess. So long as I can separate the nitrated products. I'm going to give one or two of those procedures a go!