[Chaste]

Can anyone shed some light onto this problem that I have?

my proposed solution is esterificating it, then add organometallic reagent to the ester.
is there a shorter method? and is my proposed solution correct?

[azmanam]

are you talking about elongating the chain?  Like taking propanoic acid (3 carbons) and making it n-butanol (4 carbons)?

The proposed method won't work for 2 reasons.  One, the organometallic will add to the ester twice giving a tertiary alcohol, and two you'll get (2-methyl)-2-butanol, rather than 1-butanol.

Or am I looking at it wrong?

[Dan]

are you talking about elongating the chain?  Like taking propanoic acid (3 carbons) and making it n-butanol (4 carbons)?

Based on the answer given I think we're looking at adding to the carbonyl with a carbon nucleophile, followed by reduction of the resulting ketone to the secondary alcohol.

my proposed solution is esterificating it, then add organometallic reagent to the ester.
is there a shorter method? and is my proposed solution correct?

You're on the right track, however, as Azmanam has pointed out, you will probably have problems with over-addition to the carbonyl. Problem is that the ketone you want to generate is more reactive than the ester you started with, so you will get a second addition of your organometallic reagent.

I see two options.

1. Instead of an ester, can you think of a carboxylic acid derivative that is more reactive than a ketone? This will help to control single addition, giving a ketone.

Once you have your ketone, how do you propose to reduce it to the alcohol?

2. Do the reduction first. How could you reduce your carboxylic acid to an aldehyde (more than one step may be required)?
Once you have your aldehyde, you can then add your organometallic and get your secondary alcohol.

[Chaste]

are you talking about elongating the chain?  Like taking propanoic acid (3 carbons) and making it n-butanol (4 carbons)?

Yes. I am talking about this. Chain elongation.

if I chose option 2 of what Dan proposed, can I use potassium dichromate to reduce carboxylic acid to an aldehyde? or would NaBH4 be better?

[g-bones]

If you are going to try and elongate the the chain you can convert the carboxylic acid to an acid chloride and perform an arndt-eisert homologation than treat the resulting product with a reducing agent.  Try working up with MeOH to form methyl ester and reduce with LAH or DIBAL-H which is normally thought of to stop at the aldehyde but will reduce down to the alcohol if warmed up and run in a coordinating solvent like THF. hope this helps 

http://en.wikipedia.org/wiki/Arndt–Eistert_reaction

[Dan]

are you talking about elongating the chain?  Like taking propanoic acid (3 carbons) and making it n-butanol (4 carbons)?

Yes. I am talking about this. Chain elongation.

If you're after a primary alcohol then you can ignore my suggestions, listen to g-bones

[UnintentionalChaos]

The problem with the Arndt–Eistert reaction is that it requires you to work with diazomethane, which can only be done on a very small scale with some semblance of safety.

A slightly more sane route would be to reduce the COOH functionality to the alcohol, Convert it to the alkyl halide, then prepare the grignard reagent and react it with formaldehyde. On workup, the chain-extended primary alcohol is isolated.

If you'd rather avoid the formaldehyde, you can quench the grignard with an excess of dry ice, then reduce the resulting COOH to the alcohol.

are you talking about elongating the chain?  Like taking propanoic acid (3 carbons) and making it n-butanol (4 carbons)?

Yes. I am talking about this. Chain elongation.

if I chose option 2 of what Dan proposed, can I use potassium dichromate to reduce carboxylic acid to an aldehyde? or would NaBH4 be better?

Dichromate is an oxidizing agent, and NaBH4 will not reduce COOH functionalities. Either use LAH, or treat the acid chloride with NaBH4. There are probably other ways to go about this, but those are the textbook examples.