Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: 1101 on December 01, 2010, 07:57:50 PM

Title: How to replace a carboxyl group with a methyl group?
Post by: 1101 on December 01, 2010, 07:57:50 PM

Is there any general method for replacing a carboxyl group with a methyl group, or any method of replacing the double bonded oxygen and hydroxyl group with three hydrogen atoms? Can this be done using chemicals that one can commonly buy so I can try it?

Title: Re: How to replace a carboxyl group with a methyl group?
Post by: majorjp on December 01, 2010, 08:26:01 PM

One method would be to reduce the carboxyl group via LiAlH₄ yielding an 1^o alcohol. The alcohol could then be then be eliminated by means of dehydration yielding an alkene. Which could ultimately be converted into an alkane by hydrogenation by H₂ and Pd-C. It's a roundabout method and I'm sure there is a more efficent method but I'm drawing a blank right now.

Title: Re: How to replace a carboxyl group with a methyl group?
Post by: 1101 on December 01, 2010, 11:12:43 PM

Thanks. I wouldn't exactly call the catalysts you suggested common and I wouldn't have any idea where to get them but it's a start. I might be able to find so more common equivalents.