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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: nimaesmaeilian on April 25, 2016, 02:10:50 PM

Title: Estrification
Post by: nimaesmaeilian on April 25, 2016, 02:10:50 PM

Hello every body.
I want to react the primary hydroxyl group of a long chain alkyl glucoside surfactant with an amino acid (Estrification). is there any body to help me?

Best
Nima

Title: Re: Estrification
Post by: Alwin Kristen on April 26, 2016, 01:46:59 PM

Hey, Welcome to the forum. You must show that you have tried to solve the problem by yourself before we can help you. That's the forum policy. You should read the forum rules.

Title: Re: Estrification
Post by: Unco on April 27, 2016, 01:09:04 AM

I am almost positive that you can find a procedure to do this on SciFinder.
That aside, what I would do is do a selective oxidation on that primary alcohol (since that's the only primary alcohol) into an aldehyde, then use a hydride source (maybe DIBALH) so that it adds to the aldehyde to form the negatively charged oxygen species, which then you can do an esterification to the amino acid. Note you should turn the carboxylate group on the amino acid into an ester or an acyl chloride first.

Title: Re: Estrification
Post by: Dan on April 27, 2016, 02:43:55 AM

Quote from: nimaesmaeilian on April 25, 2016, 02:10:50 PM

Hello every body.
I want to react the primary hydroxyl group of a long chain alkyl glucoside surfactant with an amino acid (Estrification). is there any body to help me?

Best
Nima

What esterification reactions do you know? Do you think you could you apply them to your system?

Some inspiration here: https://en.wikipedia.org/wiki/Ester#Preparation