Study Synthesis of Methyl Benzoate

For a more complete listing see McLafferty and Turecek (1993).  

Verify a postulated structure by comparing the spectrum with a reference spectrum. The reference spectrum may be found in the literature or it may be measured by purchasing or synthesizing a standard of the postulated structure. 

To illustrate how gas chromatography and mass spectrometry can be used to characterize the products of an organic reaction, we consider the synthesis of methyl benzoate using a base-catalyzed esterification of benzoic add.The reaction proposed for this synthesis involved deprotonation of benzoic add by n-butyllithium in dry tetrahydrofuran (THF), followed by the addition of methyl iodide, with dimethylformamide (DMF) added to promote the Sn2 displacement of iodide by the benzoate anion  

The synthetic work presented below was carried out by Joshua Fhcheco, Bowdoin College Class of 1999. 

the mass spectrum for peak 1 is consistent with the structure of methyl benzoate. We could further confirm our identification by consulting a library of mass spectra. If we had any pure methyl benzoate around, we could also prepare a standard and use both the GC retention time and the mass spectrum of the standard as a means of confirming the compound identification. 

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