[nimbus8]

I know this is more of a synthetic chemistry question but does anyone have any insights about removing a hydroxide hydroxyl group from a 4 position on a carbon ring?

{MOD Edit: proper organic terminology}

[opsomath]

I'm guessing you're in organic 1 or 2? You need to give us the structure or else describe it thoroughly. For instance, is your "carbon ring" a cyclohexane or a benzene? Are you trying to replace it with a hydrogen?

[nimbus8]

The ideal situation in this case is complete removal of the hydroxide. The carbon ring is a benzene(sorry for not clarifying that)
here is the problem i was given

[kriggy]

I thikn you can
a) reduce it with twice molar amount of HI
b) possibly substitue -OH with halogene, then use grignard reaction to get R-MgX and then just hydrolyze it in water or other protic solvent

[camptzak]

I think Na⁺H^- would work as an electrophilic aromatic substitution

[discodermolide]

Make the methanesulphonic acid ester and hydrogenate it,
see
http://www.google.ch/url?sa=t&rct=j&q=deoxygenation%20of%20of%204-hydroxyindole&source=web&cd=1&ved=0CCwQFjAA&url=http%3A%2F%2Fwww.sciencemadness.org%2Ftalk%2Ffiles.php%3Fpid%3D126146%26aid%3D5448&ei=F8SNUfOsK4msOp7JgMAF&usg=AFQjCNH5xJ36CRaOAQ2qKKYqpIGka2hzXw&sig2=zaoqP38xf9jghulX-HRw1g

[orgopete]

This strikes me as a significant synthetic challenge. There must be more to this question than what is being asked because it would be simpler to buy indole.

[nimbus8]

Nope there isnt more to the question, thank you for all of the responses.

[AC Prabakar]

I thikn you can
a) reduce it with twice molar amount of HI
b) possibly substitue -OH with halogene, then use grignard reaction to get R-MgX and then just hydrolyze it in water or other protic solvent

This could be a good option.
I just would like to share my exp. on this part.
Try to replace "-OH" with any halogen (-Cl,-Br) and try dehalogenation procedures like hydrogenation.
This option will serve the purpose under mild condition and worked in my case (not in indole but other compound with wide liable functional group)

Best of luck!