“Synthesis of Aromatic Esters”
In this lab we were aiming to synthesize three “novel” aromatic esters: propyl 4-methoxycinnamate, propyl 4-methylbenzoate, propyl 2-methylbenzoate.
These are novel in the sense, that there is currently no spectral information for these compounds in “chemspider” nor “emolecules” databases.
proton and 13 NMR spectra of Novel Aromatic_Esters.pdf
Aromatic_Esters_IR.pdf
Positive
+ Simple procedure, the emphasis was more on characterizing novel compounds.
+ The products smell okay – olfactory confirmation of a successful synthesis.
Neutral
± To my surprise, the products were liquids at room temperature. I was expecting some waxy solids.
± We added a large excess of 1-propanol to push the equilibrium towards the products.
Negative
– Our instruments and skills are pretty limited to do much characterization – I will have to outsource the MS and NMR data.
Student Comments 2008: Synthesis of Aromatic Esters
Photo Gallery:
Inquiry & Extension ideas.
● A combinatorial scheme projects the synthesis of hundreds of novel esters from carboxylic acids and alcohols ordered from Aldrich.
● Milder conditions would make the use of secondary alcohols possible.
Changes to published procedure:
- An additional purification step is needed. Vacuum distillation? Column chromatography?
Comments (1)
alicia said
at 1:33 pm on Apr 27, 2008
Even though the procedure says to add a certain amount of propanol, you may need to add more propanol so that the mixture does not dry out during reflux.
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