Chemistry-Apirin Lab, question about phenyl salicylate

[melanie55]

Homework Statement

The phenyl ester of salicylic acid, phenyl salicylate, is also a useful pharmaceutical. But phenol does not react with salicylic acid directly. Suggest a possible method to accomplish the synthesis of phenyl salicylate.

Homework Equations

This question has been included in with an aspirin lab, which is produced by esterification (a hydrocarbon alkyl and a carboxylic acid) so I would assume it is produced by esterification, however, the question states that they do not react directly.

The Attempt at a Solution

I have tried researching phenyl salicylate, however everything I find is quite short or irrelevant to what the question is asking. I'm wondering if a catalyst being used would solve the problem, or if instead of trying to react phenol, another phenyl compound is used. I'm not certain if there is a specific phenyl compound that I should suggest, or if answering that a phenyl compund should be used instead of phenol.
If anyone knows more on te subject, it would be very much appreciated!
thanks

 

[melanie55]

After sleeping on it, I'm wondering if maybe mixing the phenol with the acetylsalicylic acid may work.

 

[melanie55]

Each source I go to for the synthesis of phenyl salicylate says that it is formed by phenol and salicylic acid. Not very helpful. However one site says that it is formed by heating phenol and salicylic acid with a catalyst. This is slightly different than what the other sources are saying, and I'm not sure if it fits the requirements of the question. If a catalyst and heat are used, does that mean the two reactants are not reacting directly?

 

[chemisttree]

Try thinking of phenol as an alcohol and saflicylic acid as a carboxylic acid. How are esters formed from these two species?

 

[melanie55]

I actually found the answer yesterday, but thanks for helping :)
It had something to do with turning phenol into the ionic compound sodium phenoxide. There's also another method with combining two dehydrated salicylic acid molecules (salicylic anhydride) to react with phenol and produce phenyl salicylate.

 

[Keladry]

It seems I am doing either the same lab as you or one that is really similar, and i have run into the same problem. Would you mind posting a link to the site where you found the two methods? It would be GREATLY appreciated!

 

[melanie55]

Gosh I completely forgot about this. It was several years ago. I'm not really sure where I got it from, but I still have my bibliography from the lab. You can look through the sources to find it.

1. Aspirin Foundation of America. (2007). Aspirin Foundation Homepage. Retrieved March 6, 2007. Available:http://www.aspirin.org/history.html [Broken] (ASP)

2. Clark, Jim. (2004). Preparation of Esters. Retrieved March 8, 2007. Available: http://www.chemguide.co.uk/organicprops/esters/preparation.html#top
(EST)

3. Samter, Max. (1997). McGraw-Hill Encyclopedia of Science and Technology. 8th Edition (Vol. 2). USA: McGraw-Hill (MGH)

4. Wiley, John. (2006). Aspirin. Retrieved March 6, 2007. Available: http://www3.interscience.wiley.com:...r/0471661791/cutting_edge/aspirin/aspirin.htm (WIL)

5. Schneider, R.F. (2006). Synthesis of Aspirin. Retrieved March 12, 2007. Available: http://www.sinc.sunysb.edu/Class/che134/susb/susb028.pdf (SCH) picture from here

6. Oklahoma State Uni. (2006). Synthesis of Aspirin. Retrieved March 8, 2007. Available: http://intro.chem.okstate.edu/ChemSource/medicine/lab1.htm (OKL)

7. Lide, D. (Ed.). (2003-2004). CRC Handbook of Chemistry and Physics. USA: CRC Press, LLC. (CRC)

Good luck with the lab!

 

[Keladry]

Thank you SO much!