[EngPet]

Oleic acid is C18 fatty acid reacts with alkanolamines like monoethanolamine easily to form surfactants According to reactivity the NH2 is more reactive than OH to react with acids so oleic acid amide formation is the main product than oleic acid esterification reaction

My question how to synthesize ester of oleic acid with monoethanolamine or in other words how to protect and deprotect the NH2 in monoethanolamine to make the esterification to be the main route Without hydrolyzing the product
what I need
Oleic acid + monoethanolamine = 2-Aminoethyl oleate
https://en.wikipedia.org/wiki/Oleic_acid
https://en.wikipedia.org/wiki/Ethanolamine
https://pubchem.ncbi.nlm.nih.gov/compound/6436599#section=Top
http://gulf-up.com/do.php?img=121435

thanks in advance

[phth]

no need for a protecting group.  Kinetic and thermodyamic control lead to two products.  Deprotonate with a strong base such as NaH and do the reaction cold.  Practice using Scifinder to find a written procedure.

[EngPet]

I need suggested procedure as I dont have access to Scifinder

[wildfyr]

I saw two different approaches which leap out at me on scifinder.

Add oleic acid and ethanolamine together in toluene, then add thionyl chloride. The thionyl chloride will react with the carboxylic acid first and produce HCl, protonating the amine, and the alcohol can then react with the acid chloride. (http://www.google.com/patents/CN104086458A?cl=en)

The other way was basically fischer using sulfuric acid and the same concept of keeping the amine protonated. Their procedure was to make the acetyl version. ethanolamine HClsalt+acetic acid +1 drop sulfuric acid refluxed for two hours, then a precipitation and recrystallization to get the product. http://www.nrcresearchpress.com/doi/pdf/10.1139/v67-321 (look for the entry starting with "Ethanolamine hydrochloride")