Chemical Forums
1 Hour
1 Day
1 Week
1 Month
Forever
December 23, 2024, 06:19:48 AM
Forum Rules
: Read This Before Posting
Home
Help
Search
Login
Register
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
Conversion of a -OR group to a -OH group
« previous
next »
Print
Pages: [
1
]
Go Down
Topic: Conversion of a -OR group to a -OH group (Read 2813 times)
0 Members and 1 Guest are viewing this topic.
majorjp
Regular Member
Posts: 35
Mole Snacks: +0/-2
Conversion of a -OR group to a -OH group
«
on:
October 13, 2010, 03:53:12 PM »
I look everywhere to find a mechanism for this reaction and couldn't find anything. My best guess is to treat the -OR group with HBr to form an alkyl halide and then treat with a NaOH solution but I'm not entirely sure, or if there"s an easier way please let me know. Thanks
Logged
Doc Oc
Chemist
Full Member
Posts: 564
Mole Snacks: +48/-12
Re: Conversion of a -OR group to a -OH group
«
Reply #1 on:
October 13, 2010, 06:00:56 PM »
This is very substrate dependent, so -OR to -OH isn't enough information. Is this an aromatic ether?
Logged
majorjp
Regular Member
Posts: 35
Mole Snacks: +0/-2
Re: Conversion of a -OR group to a -OH group
«
Reply #2 on:
October 13, 2010, 06:35:50 PM »
The molecule in question is
[19,20-
13
C]-17a-ethinyl-estra-1,3,5-triene-3,17B-diol
I was reviewing its synthesis and got to the final step which is the conversion of the -OR group to the -OH group located on C3 on the benzene ring in the structure but unfortunately I just couldn't seem to figure it out.
A picture of the structure can be found at:
http://keur.eldoc.ub.rug.nl/FILES/wetenschappers/10/461/461.pdf
At the bottom of page 2
Logged
Doc Oc
Chemist
Full Member
Posts: 564
Mole Snacks: +48/-12
Re: Conversion of a -OR group to a -OH group
«
Reply #3 on:
October 13, 2010, 06:44:46 PM »
For those types of deprotections I've typically seen drastic conditions (HI, BBr3). But it works the way you think it does, alkyl halide is formed. According to that paper the product is purified via chromatography.
Logged
majorjp
Regular Member
Posts: 35
Mole Snacks: +0/-2
Re: Conversion of a -OR group to a -OH group
«
Reply #4 on:
October 13, 2010, 06:47:02 PM »
That's what I concluded as well but I figured it best to check. Thanks
Logged
Print
Pages: [
1
]
Go Up
« previous
next »
Sponsored Links
Chemical Forums
Chemistry Forums for Students
Organic Chemistry Forum
Conversion of a -OR group to a -OH group