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Synthesis of Benzaldehyde from Toluene in 20 Minutes

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First published at 12:48 UTC on October 3rd, 2019.

#gbl
#benzaldehyde
#toluene

poormanschemist

PoorMansChemist

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In this video I explore the oxidation of toluene to benzaldehyde using barium ruthenate with glacial acetic acid in dichloromethane using a ferric chloride catalyst at the ambient air temperature. The mixture is allowed to react for 20 minutes and then it is tested for the presence of benzaldehyde with Bradys Reagent and Jones Reagent. Both reagents yielded a positive test for the aldehyde. According to the paper this reaction has broad utility and even the uncatalyzed version is able to oxidize THF to GBL in 30 minutes in 64% yields at 23 C and cyclohexane to cyclohexanone in 240 minutes with a 60% yield.

You can download the paper I took this reaction from at http://sci-hub.tw/ The paper is called "Oxidation of Alkanes by Barium Ruthenate in Acetic Acid: Catalysis by Lewis Acids" by Tai-Chu Lau and Chi-Keung Mak. Enjoy! :-)

Website: www.poormanschemist.com

Addendum: At 19:02 the subtitle should read "As it turns out the organic and aqueous layers do separate. However the aqueous layer has a large volume making isolation of the organic fraction difficult."

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