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Topic: Questions about 4-acetylaminobenzoic acid!  (Read 10098 times)

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Tidus

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Questions about 4-acetylaminobenzoic acid!
« on: August 13, 2005, 12:38:13 AM »
Umm okay,
Is there another way to make 4-acetylaminobenzoic acid from 4-aminobenzoic acid (aka. PABA) without using acetic anhydride?

Also can someone give me data of wheather 4-acetylaminobenzoic acid is soluble in acid and in base.

Thanks to people that can *delete me*  :)

Offline HP

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Re:Questions about 4-acetylaminobenzoic acid!
« Reply #1 on: August 13, 2005, 05:58:15 AM »
I think you can also use Acethyl chloride/Pyridine as acetylating agent. Not sure for the solvent of PABA may be DMF or toluol.
xpp

Tidus

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Re:Questions about 4-acetylaminobenzoic acid!
« Reply #2 on: August 13, 2005, 08:18:34 AM »
hmm interesting.. thanks for that..
if anyone else wants to add something, plz do!  :)

laotree

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Re:Questions about 4-acetylaminobenzoic acid!
« Reply #3 on: August 13, 2005, 08:30:02 PM »
Schotten-Baumann acylation might be the best condition of you case.
The amine (1 equiv.) was dissolved into methylene chloride . 2 M NaHCO3 aqueous solution  was added into the solution. The mixture was stirred vigorously, and then acid chloride (1.5 equiv.) in methylene chloride was added into the mixture slowly. The mixture was stirred for 2 hours. The organic layer was separated, and washed with Na2CO3 aqueous solution three times. The resulting organic layer was dried, and concentrated. The resulting residue was separated by silica gel column. Schotten-Baumann reaction is very good for the acylation of unreactive amine. Weak bases, like RCOOK also could catalyze the acylation between acid chloride and unreactive amine.
Borrowed from ecompound.com

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