UnintentionalChaos - 14-4-2007 at 17:49
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.
leu - 14-4-2007 at 18:02
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)
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UnintentionalChaos - 14-4-2007 at 18:10
I used the "fucking google", but didn't find anything specific enough with a number of search strings. Thanks, though.
jon - 14-4-2007 at 23:48
a throwback to the old utfse huh?
garage chemist - 15-4-2007 at 08:14
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.
chemrox - 20-4-2007 at 19:16
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.