ORGLIST: Removal benzyl protecting group

Date view Thread view Subject view Author view Attachment view

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

__________________

ORGLIST - Organic Chemistry Mailing List
Website / Archive / FAQ: http://www.orglist.net/
List coordinator: Joao Aires de Sousa (jas$##$mail.fct.unl.pt)

Date view Thread view Subject view Author view Attachment view

This archive was generated by hypermail 2.1.4 : Fri Sep 19 2003 - 12:16:54 EDT