[Baerchen]

Hi there,

I seem to have problems identifying how to convert a primary halogen to a hydroxyl group. I thought it would be straightforward but it seems going the other way is the more common reaction.
Ideally I'd like to convert the halide to hydroxyl, aldehyde or carboxylic ester so if I can get directly to any of these I would be happy.
I am thinking about the Williamson-ether synthesis to make an ether and go from there.

I appreciate any suggestions of reagents or even some better search terms to help me with.

Thank you!

[Doc Oc]

Depending on your alkyl halide this can be a tricky reaction.  The most obvious solution would be to add NaOH, but you risk not only getting the substituted product, but also the eliminated product.

If you want to convert it to a carboxylic acid you could try turning your alkyl halide into a Grignard and reacting it with CO2, although that also depends on the complexity of your starting material.

[Baerchen]

Thanks for your answer, J-bone.
I do indeed have a complicated structure, so I will research which of these methods (if any) will be suitable.
Thanks again for giving me some direction!

[stewie griffin]

The Kornblum oxidation will give you the aldehyde...
http://en.wikipedia.org/wiki/Kornblum_oxidation

[azmanam]

also, careful with the Grignard + CO2 route, you'll extend the carbon chain by 1.

You could use sodium acetate as your nucleophile, instead of sodium hydroxide. 

[Doc Oc]

also, careful with the Grignard + CO2 route, you'll extend the carbon chain by 1.

You could use sodium acetate as your nucleophile, instead of sodium hydroxide. 

Oops!  Good catch, azmanam!

[OC pro]

One could also eliminate the halide to afford the olefine (only when there is no possibility for isomerisation) which could then underwent hydroboration to the primary alcohol,

[Baerchen]

Great, thanks for all of your suggestions. The Kornblum oxidation seems to suit my needs and I hadn't heard of it before so thanks! I've found some recent reports on this type of reaction that sound promising. I'll report back with my results! Thanks again for your help