[xaxax]

Dear members
I want to make a reaction by using an amino alcohol (ethanol amine or 3-amino-1- propanol) and a fatty acid mixture (oleic acid, linoleic acid stearic acid).
I want to make the reaction only between amino and carboxylic groups, therefore, at the end of the reaction I hope to obtain an amide that contain a hydroxyl group. How can i do this reaction?
I am waiting for your replies and opinions.

[OC pro]

Suitable protection of the alcohol, e. g. as silyl ether. Then coupling. Then protodesilylation.

[contra]

Protect the alcohol with tert-butyldimethylsilyl linkage, mix this product with the fatty acid to yield the amide, deprotect the silyl ether with fluoride ion.

Edit: Didn't see OC already posted essentially the same thing at the same time, sorry for redundancy

[xaxax]

thanks for your replies. since i am amateur for this website, i dont know everything. Also, i am very new in chemistry, therefore, i need your experiences.
Thanks very much.

[xaxax]

if i dont carry out alcohol protection and deprotection, what happens? ester bond, amide bond, both ester and amide bond???
could you give me some information?

[AC Prabakar]

if i dont carry out alcohol protection and deprotection, what happens? ester bond, amide bond, both ester and amide bond???
could you give me some information?

May i know the procedure you would like to use?(methodology with reagent?)
Because if you use any specific amidation procedure(which is having tolerability over alcohol substrate),then protection of alcohol is not necessary(Forgive me as i don't know the availability of selective amidation over alcohol substrate! Let me check this parallely!!).

But in general method, you may end up with some undesired reaction which may lead to undesired products along with your desired product.
 In this case, you may have the following problems:

1.Purification of obtained mixture to obtain pure product
2.Loss of compound in the form of impurities(undesired product)
 For the propable undesired Reaction/product refer the attachment.

[xaxax]

if i dont carry out alcohol protection and deprotection, what happens? ester bond, amide bond, both ester and amide bond???
could you give me some information?

May i know the procedure you would like to use?(methodology with reagent?)
Because if you use any specific amidation procedure(which is having tolerability over alcohol substrate),then protection of alcohol is not necessary(Forgive me as i don't know the availability of selective amidation over alcohol substrate! Let me check this parallely!!).

But in general method, you may end up with some undesired reaction which may lead to undesired products along with your desired product.
 In this case, you may have the following problems:

1.Purification of obtained mixture to obtain pure product
2.Loss of compound in the form of impurities(undesired product)
 For the propable undesired Reaction/product refer the attachment.

This was very useful for me. I don’t know whether amide can be selected from the reaction mixture at the end of the reaction.
I want to explain my condition, I have a monomer containing hydroxyl group. This monomer turns into polymer with curing and when it is polymer, it is very brittle. Therefore, I have to give it flexibility, I was told to make this reaction by using fatty acids.
I considered and then, I decided to link the hydroxyl group of the monomer to the para position of TDI (toluene diisocyanate) and fatty acid to the orto position of TDI, but there was a big problem with TDI and fatty acid. They do not react easily and need high temperatures which is unwanted because of my monomer. When I reacted TDI and fatty acid, almost the fifty percent of fatty acid was unreacted, but isocyanate was consumed.
After I could not achieve this reaction, I trended to make a product containing hydroxyl group from the fatty acids. Then, I will make a reaction with the hydroxyl group of this product and TDI.
Could you offer me a short and good way: I want to make a product that contains a hydroxyl group by using fatty acids. I know there are some reactions like reduction of carboxylic acids and hydrogenation of carboxylic acids. However, as far as I see these are very hard and need very high pressure. I have to make my product in an easy way.
I hope that you understand my condition.

[Doc Oc]

I agree with AC Prabakar, you will not need to protect the alcohol if you want the amine to react, it is significantly more nucleophilic.  I have protected the amine of serine successfully without affecting the alcohol.

[xaxax]

do you have information about the catalyst type and temperature for the reaction between isocyanates and primary amines?
i know only molecular sieves for catalyst type.
the reaction can be carried out at 140-160C without solvent for 2-3 hours.
do you have a good pathway for amine and isocyanate reaction?