ORGLIST: reply: synth of 3-methylsalicylic acid

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From: Amanda Lucille Kohnen (kohnen$##$MIT.EDU)
Date: Thu Jul 17 2008 - 14:03:54 EDT


3-methylsalicylic acid is commercially available for very cheap
($76/500g from TCI). I would prefer to buy it.

If you want to synthesize it from scratch, I would suggest starting
with 2-methyl phenol (aka o-cresol which costs approx $29/500g from
TCI) and treating it with NaOMe/MeOH to form the sodium phenoxide,
then (to do electrophilic aromatic substitution) stir o.n. under CO2
(to do electrophilic aromatic substitution) followed by acidic work
up. I don't know the exact conditions (equiv, temp, etc), but you
could look it up. Make sure everything is anhydrous!
This process is known as the Kolbe-Schmitt reaction and you may find a
detailed experimental in the patent US2006183939.

Good luck,
Lucy

On Jul 17, 2008, at 12:00 PM, everybody-request$##$orglist.net wrote:
>
> Message: 1
> Date: Thu, 17 Jul 2008 03:26:22 -0700 (PDT)
> From: Gufranuzzaman Khan <gufranuz$##$yahoo.com>
> Subject: Re: ORGLIST: Triethylamine hydrochloride
> To: everybody$##$orglist.net
> Cc: saswatil$##$hotmail.com
> Message-ID: <53636.14647.qm$##$web45216.mail.sp1.yahoo.com>
> Content-Type: text/plain; charset="utf-8"
>
> Dear all
> What is raw materials used for making 3-methyl salicylic acid.
> ?
> Dr. Emran
>
> --- On Wed, 2/7/08, Saswati Lahiri <saswatil$##$hotmail.com> wrote:
>
> From: Saswati Lahiri <saswatil$##$hotmail.com>
> Subject: Re: ORGLIST: Triethylamine hydrochloride
> To: everybody$##$orglist.net
> Date: Wednesday, 2 July, 2008, 6:20 PM
>
>
>
>
> #yiv467427568 .hmmessage P
> {
> margin:0px;padding:0px;}
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>
> What is your solvent? We separate it from dry acetone.
> Saswati
>
>
>
>
>
>
>
> Date: Tue, 1 Jul 2008 14:29:41 -0500
> From: sunil.orgchem$##$gmail.com
> To: everybody$##$orglist.net
> Subject: ORGLIST: Triethylamine hydrochloride
>
>
>
> Hi,
> ??? Does any know the best way?to get rid of all the triethylamine
> hydrochloride from reaction mixture ?
> ?
> Thanking You,
> Sunil?
>
>
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Amanda Lucille Kohnen

PhD Candidate
Department of Chemistry
77 Mass Ave., Rm 18-263
Cambridge, MA 02139
kohnen$##$mit.edu
phone: 617-253-1835
fax: 617-252-1504


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