[AWK]

Schotten Baumann reaction is usually performed in temperature close to 0 C (ice) with some excess of acetyl chloride. Yields are usually high concerning amines

[lutesium]

But if its a conc. NaOH solution it can be cooled up to -15-20°c I guess; so it won't be ice!!!

But AWK can you explain me what does a weak amine means???


Lutesium...

[AWK]

Compare Kb of ammonia and aniline

[lutesium]

Ahhh... You are saying that the basicity of an amine determinates its strength so if an amine is stronger can it be acylated easier??? For example can ammonia be acylated with Et-O-Ac to produce AcetylAmine??? Or the reverse??? I'm really puzzled please *delete me*!!


Lutesium...

[Butyllithium]

I think it will be work, but need more violent conditions(e.g.high temp. or sealed in tube).
I have ever prepared a secondary alcohol, which had been extracted from water with Ethyl acetate. When the extraxts were concentrated under reduced pressure,transesterification reaction occured.
Due to more basic/nucleophilic than aliphatic achohol, aniline will react with EtOAc in same conditions.