UnintentionalChaos
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Hydrolysis of ASA
Simple question, but does anyone have a general idea of how easily acetylsalicylic acid is hydrolyzed with NaOH? I have a beaker of 1 part (molar
parts) ASA and 2 parts NaOH and am unsure if heating is necessary to break the ester bonds, given how easily ASA is usually mentioned to hydrolyze,
breaking down somewhat even in moist air.
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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leu
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You should find this experimental handout from the University of Oregon somewhat helpful, you could have used the fucking Google yourself 
Attachment: AspAnalysis.pdf (276kB)
This file has been downloaded 33706 times
Chemistry is our Covalent Bond
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UnintentionalChaos
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I used the "fucking google", but didn't find anything specific enough with a number of search strings. Thanks, though.
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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jon
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a throwback to the old utfse huh?
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garage chemist
chemical wizard
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Why do you use NaOH for hydrolysis? Wouldnt it be more convenient to use dilute HCl, as you can monitor the hydrolysis by smelling the reaction mix,
the smell of acetic acid will get stronger and stronger as it progresses. The hydrolysis is irreversible with HCl too, as salicylic acid can only be
acetylated in anhydrous environment.
Then you would only need to cool down to crystallize pure salicylic acid, instead of having to acidify as with NaOH.
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chemrox
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Applause to Garage Chemist for his comments and a caution to Lieu for his. Google is not consistent and we all have days when we miss the obvious.
This is one of the many reasons, although perhaps not the best, for having an open discussion group. We should be kind to one another here. There's
no cost and we would all feel better.
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