ORGLIST: Re: Everybody Digest, Vol 11, Issue 14

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From: Lakshmipathi Pandarinathan (plpathi$##$hotmail.com)
Date: Tue Aug 23 2005 - 19:00:27 EDT


Ruisong Xu

try heating the compound in neat formic acid for 30 min. you could use the
boiling temperature of formic acid or even lower temperature ca., room
temperature and this depends upon the substrate. good luck
cheers
Pathi

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Subject: Everybody Digest, Vol 11, Issue 14


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> 1. deprotection of the ethylene glycol protected 2, 4,
> 6-tricyanobenzyl aldehyde (Ruisong Xu)
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> Message: 1
> Date: Mon, 22 Aug 2005 23:08:31 -0500
> From: "Ruisong Xu" <rsxu$##$siu.edu>
> Subject: ORGLIST: deprotection of the ethylene glycol protected 2, 4,
> 6-tricyanobenzyl aldehyde
> To: <everybody$##$orglist.net>
> Message-ID: <001301c5a798$53f52710$a16ce683$##$Ruisong>
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> Hello, everyone,
>
> Just wondering if anyone can help me to figure out how to deprotect the
> ethylene glycol protected 2,4,6-tricyanobenzyl aldehyde. Seems to be an
> easy reaction. However, I tried to use tosylic acid, HCl, AlCl3+
> N,N-dimethyl aniline, or I2 with acetone to cleave it but none was
> successful. But the ethylene glycol protect 2,4,6-tribromobenzyl aldehyde
> can be deprotected pretty easily by tosylic acid in acetone. Please give
> me some advice if anyone ever had similar experience. Thanks a lot.
>
> Ruisong Xu
>
> Department of Chem. and Biochem.
> Southern Illinois University at Carbondale
> Carbondale, IL 62901
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