Re: ORGLIST: Removal benzyl protecting group

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From: Uno Mäeorg (uno$##$chem.ut.ee)
Date: Fri Jan 25 2002 - 07:25:29 EST

Hi Bert!

If it's really so as you wrote, then it seems to be the case when catalyst
is poisoned. I guess you have to purify first the starting material (benzyl
derivative) and then the hydrogenolysis will be OK.
Good luck.

Uno

At 10:05 23.01.02 +0000, e.kruiswijk$##$btinternet.com wrote:
>Dear All,
>
>Starting with solketal (protected glycerol) I make the benzylic ether,
>followed by hydrolysis of the isopropylidene group with amberlite. I do a
>DCC/DMAP mediated esterification and purify the product. When I want to
>remove the benzyl group using palladium on coal and hydrogen I find that I
>cannot remove the protecting group. This only happends when I use a DCC/DMAP
>esterification, in every other case I can remove the benzyl group.
>Is there someone who has an idea what is going on here? I really like to use
>the DCC/DMAP esterification procedure above other methods.
>
>
>Thank you.
>
>
>Bert Kruiswijk
>
>
>
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>

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