Ferdinand Tiemann – co-discoverer of Reimer-Tiemann reaction, jonon compound synthesis

Ferdinand Tiemann – co-discoverer of Reimer-Tiemann reaction

Reimer-Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols
Ferdinand Tiemann

Biography & contributions

Ferdinand Tiemann, a German chemist born on June 10, 1848 – died on November 14, 1899. Tiemann’s major works include discovering Reimer-Tiemann reaction, synthesis of jonon compound, synthesis of vanillin from coniferyl alcohol.

Tiemann is also best known for his discovery of Tiemann rearrangement.

Facts about vanillin

Vanillin is an organic phenolic aldehyde compound. It is having aldehyde, hydroxyl and ether as functional groups in its structure. Vanillin was first isolated from vanilla pods by Nicolas-Theodore Gobley in 1858.

In 1874, the German scientists Ferdinand Tiemann and Wilhelm Haarmann deduced its chemical structure, at the same time finding a synthesis for vanillin from coniferin, a glucoside of isoeugenol found in pine bark.

Vanillin is most prominent as the principal flavor and aroma compound in vanilla. Cured vanilla pods contain approximately 2% by dry weight vanillin. The biosynthesis of vanillin is achieved by the conversion of tyrosine into 4-coumaric acid then into ferulic acid and finally into vanillin. Vanillin is then converted into its corresponding glucoside.

Vanillin is as a flavoring, usually in sweet foods. It is also used in the fragrance industry, in perfumes, and to mask unpleasant odors or tastes in medicines, livestock fodder, and cleaning products. Vanillin has been used as a chemical intermediate in the production of pharmaceuticals and other fine chemicals. Vanillin-HCl staining can be used to visualize the localisation of tannins in cells.

Reimer-Tiemann reaction

The Reimer-Tiemann reaction is an organic reaction used to convert a phenol to o-hydroxy benzalde-hyde using chloroform. The Reimer-Tiemann reaction mechanism begins with abstraction of the proton from chloroform with the base to form a trichlorocarbanion which spontaneously loses a chloride ion to form a neutral dichlorocarbene. The base is also deprotonates the phenol reagent which then attacks the carbene. A series of steps and a final acid work-up result in the o-hydroxy benzaldehyde product.

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