ORGLIST: Removal benzyl protecting group

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From: e.kruiswijk$##$btinternet.com
Date: Wed Jan 23 2002 - 05:05:15 EST


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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