Author Topic: CH3-C6H5SO2*CH3O - an OTC methylating agent?  (Read 2835 times)

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Chromic

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Re: CH3-C6H5SO2*CH3O - an OTC methylating agent?
« Reply #20 on: January 25, 2002, 05:48:00 AM »
I've read a patent and scaled everything accordingly, does this seem OK:

32.8g 94% sulfuric acid
10.0g toluene

reflux at 115C, until toluene reacts (apx how long? couple hours?), cool to room temp

add 2.5g water down the condenser

filter off ~11.3g toluene-4-sulfonic acid

Will the H2SO4 eat through standard filter paper? Is there anything I can use to wash the crystals? Btw, will some MeOH in the toluene form the methylating ester that you desired?

Antoncho

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Re: CH3-C6H5SO2*CH3O - an OTC methylating agent?
« Reply #21 on: January 25, 2002, 08:28:00 AM »
>I've read a patent

Which one? Here's the

source article for my experiment

(http://moonlight.ionichost.com/toluenesulfonic.htm)

>reflux at 115C,

not really reflux, just near boiling/barely boiling - cause when you shake it it's gonna boil violently.

>until toluene reacts (apx how long? couple hours?)

yep. You'll see when it stops.

>add 2.5g water down the condenser

Whut???

>filter off ~11.3g toluene-4-sulfonic acid

no way.

>Will the H2SO4 eat through standard filter paper?

it definitely will, in no time

>Is there anything I can use to wash the crystals?

I dunno. If you do everything like in the article, they'll bee already quite pure.

>Btw, will some MeOH in the toluene form the methylating ester that you desired?

Seemingly, no, as SWIM had no luck doing it w/methanol. Ah, everything may bee - like he just did smth wrong or had wet methanol - SWIM was unforgivingly careless at the time, now life has taught him some precision :) .

Antoncho