[accolay]

Hello all,

I have a quick question regarding synthesis. What would be the product should phthalic acid and acetic anhydride be refluxed. The crystals were recrystallized in chloroform.

I'm not sure what the product would be for an aromatic dicarboxylic acid and an acid anhydride. Any help will be appreciated.

Many thanks,
AC

[nj_bartel]

If I had to guess, I'd say it would probably lead to mostly mono-Fischer esterification, due to how one hydroxyl strongly coordinates to the other carbonyl, but I would think you could also potentially get the diesterification, depending on the conditions you used.

[accolay]

Thanks for you rapid response!  But what would be the product of the overall rxn? What ester would form? I'm going back to the lab tomorrow to do some more tests but would like to know what it is that forms with the acetic anhydride and phtalic acid.

Many thanks again for your help.  I really appreciate it,
AC

[azmanam]

phthalic anhydride?  Are you giving us all the information?  you just heated phthalic acid and acetic anhydride neat in a flask?  no solvent or any other reagents?

I doubt it's fischer, no alcohols in solution.

As for predicting the product yourself... what elements/functional groups are nucleophiles?  Which ones are electrophiles?

[accolay]

My first guess was phthalic anhydride but I wasn't sure. Didn't think it was Fischer either. I, indeed, added phthalic acid and acetic anhydride and refluxed it. Then I collected crystals and recrystallized it in chloroform, given guidelines by my research advisor.

Does this help?

Thanks for your help,
AC

[azmanam]

yes it helps.  My guess stands until you get a mp.  It's still a good exercise to go over how to predict this product.  Can you identify possible nucleophiles/electrophiles?

[accolay]

Melting point in mid-high 120s, will be going back to the lab tomorrow to redo/make sure. Thanks!

[nj_bartel]

Sorry on the Fischer - brain fart!