Chemical Forums
1 Hour
1 Day
1 Week
1 Month
Forever
November 25, 2024, 11:13:09 PM
Forum Rules
: Read This Before Posting
Home
Help
Search
Login
Register
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
Transesterification
« previous
next »
Print
Pages: [
1
]
Go Down
Topic: Transesterification (Read 3073 times)
0 Members and 1 Guest are viewing this topic.
IoanaD
Regular Member
Posts: 11
Mole Snacks: +1/-0
Transesterification
«
on:
November 15, 2009, 03:43:21 AM »
I know that transesterification of isopentenyl acetate to isoamyl acetate can be done with an acid and another alcohol that replaces the first R group. However, i am asked
what other way
we can perform the same transformation. Is there a way of reducing that double bond without touching the carbonyl? I was even thinking of protecting it via a bifunctional alcohol and then adding H2/Pd in order to selectively reduce the double bond.
Is there any other way of achieving this?
Logged
Enantiomer
Regular Member
Posts: 29
Mole Snacks: +2/-0
Re: Transesterification
«
Reply #1 on:
November 15, 2009, 04:52:05 AM »
you're right on the money, you can protect the ketone via acetal formation and then add a selective catalst (I think LiAlH
4
, I think H
2
Pd would accomplish this, as would LiAlH
4
(I'm not 100% about this one, and since it is very difficult to handle in the lab H
2
Pd would be the better choice either way)
http://en.wikipedia.org/wiki/Protecting_group
Logged
Arctic-Nation
Chemist
Full Member
Posts: 265
Mole Snacks: +33/-9
Re: Transesterification
«
Reply #2 on:
November 15, 2009, 12:15:08 PM »
No. This is an ester we're talking about, not a ketone, so protecting groups are out. The easiest way to reduce double bonds is some noble metal/hydrogen combination. Most of those won't touch the ester functionality, unlike hydride reagents.
Logged
movies
Organic Minion
Retired Staff
Sr. Member
Posts: 1973
Mole Snacks: +222/-21
Gender:
Better living through chemistry!
Re: Transesterification
«
Reply #3 on:
November 21, 2009, 05:13:15 PM »
Also, LiAlH
4
will not reduce isolate C–C double bonds (it would reduce the ester, however). H
2
+ Pd/C is the way to go for this one.
Logged
Print
Pages: [
1
]
Go Up
« previous
next »
Sponsored Links
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
Transesterification