Monthly Archives: September 2013

Benz But Doesn’t Break. Part IV

The second part of the modified benzilic acid synthesis project was as straightforward as the first part was complicated. The quantities of ammonium nitrate for the copper(II) acetate catalyzed oxidation were adjusted for the different molecular weight of the starting material. Other than that conditions were the same as for the benzoin to benzil transformation. […]

Benz But Doesn’t Break. Part III

The thiamine catalyzed coupling reaction of 4-methylbenzaldehyde created an off-white solid product. Upon analysis the product contained one to three different peaks in the GC-FID that corresponded to the coupled products. After the oxidation step was completed, one of the three peaks remained. It is reasonable to conclude that the peak after oxidation was 4,4’-dimethylbenzil. […]

Benz But Doesn’t Break. Part II

We set up the condensation reactions with the same molar quantities and under the same conditions as we had done the thiamine catalyzed benzoin reactions as few weeks before. It soon became apparent that the condensation of anisaldehyde was not occurring to any extent and the condensation of tolualdehyde was occurring much slower than it […]

Benz But Doesn’t Break. Part I

I wanted to do a variation of the Benzaldehyde to Benzilic Acid synthesis as our final project. The premise was simple: We would use derivatives of benzaldehyde for the reaction. This is a common way to explore synthetic reactions. Many articles that feature synthetic reaction have dozens of experiments done by varying the structural characteristics […]

A Case of the Benz. Part IV

Benzil to Benzilic acid The third step of the benzaldehyde to benzilic acid synthesis is the base catalyzed rearrangement of benzil to benzilic acid. An early study of this reaction was reported in a 1921 J. Am. Chem. Soc. article by Arthur Lachman. According to the procedure we followed, the reaction only required 15 minutes […]