RE: ORGLIST:An esterification that will not proceed!

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From: Yuehui Zhou (yuehuizhou$##$hotmail.com)
Date: Thu Sep 12 2002 - 09:34:01 EDT


Why not use dehydrating reagents? Are they too expensive? There is a new
kind of dehydrating reagent based on phosphorane compounds:

R3P=CZ2 + ROH + R"COOH -------> R3P=O + CH2Z2 + R'OOCR"

both byproducts can be washed away with whater.

Y. Zhou
Phosphine Technology
Cytec Canada

>From: Badru Nsubuga <bdnsubuga$##$yahoo.co.uk>
>To: Jim Mitchell <j_mitchell$##$cerilliant.com>,"everybody$##$orglist.net"
><everybody$##$orglist.net>
>Subject: RE: ORGLIST:An esterification that will not proceed!
>Date: Wed, 11 Sep 2002 22:55:39 +0100 (BST)
>
>Using 2 eq of sulfuric acid gave excellent yield of
>vanilic acid ethyl ester after cooking for 16 hours.
> I was also able to make syringic acid ethyl ester
>using the the same trick. Thanks .
>
>Badru
>
>
>
> Jim Mitchell <j_mitchell$##$cerilliant.com> wrote: > You
>should try 2eq of H2SO4 and reflux overnight,
> > that should do the trick.
> >
> > Jim Mitchell
> > Cerilliant Corporation
> >
> > -----Original Message-----
> > From: Badru Nsubuga [SMTP:bdnsubuga$##$yahoo.co.uk]
> > Sent: Saturday, September 07, 2002 5:10 PM
> > To: everybody$##$orglist.net
> > Subject: ORGLIST:An esterification that will not
> > proceed!
> >
> >
> > Reaction of 4-hydroxy-3-methoxybenzoic acid
> > (vanillic
> > acid, VA) with absolute ethanol in the presence of
> > catalytic amounts of sulfuric acid, will not produce
> > enough ethyl-4-hydroxy-3-methoxybenzoate! Does
> > anyone
> > know why? What is the pKa of VA?
> >
> > Save me that trip to the library! Thanks.
> >
> > Badru
> >
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