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Topic: Functionalization of 1-naphthylacetic acid  (Read 2197 times)

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Offline zuriel

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Functionalization of 1-naphthylacetic acid
« on: April 18, 2016, 11:09:32 AM »
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!

Offline sjb

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Re: Functionalization of 1-naphthylacetic acid
« Reply #1 on: April 18, 2016, 11:49:48 AM »
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

Offline zuriel

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Re: Functionalization of 1-naphthylacetic acid
« Reply #2 on: April 18, 2016, 02:18:05 PM »
Thank you very much, that document is VERY helpful!!

Offline wildfyr

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Re: Functionalization of 1-naphthylacetic acid
« Reply #3 on: April 18, 2016, 05:33:06 PM »
Boiling it in sulfuric/nitric acid is pretty much guaranteed to nitrate it. The trick is how many times the ring gets nitrated

Offline zuriel

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Re: Functionalization of 1-naphthylacetic acid
« Reply #4 on: April 19, 2016, 05:28:08 AM »
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!


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