[majorjp]

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

[Doc Oc]

This is very substrate dependent, so -OR to -OH isn't enough information.  Is this an aromatic ether?

[majorjp]

The molecule in question is
[19,20-¹³C]-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

[Doc Oc]

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.

[majorjp]

That's what I concluded as well but I figured it best to check. Thanks