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Mandelic acid synthesis

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    This a-hydroxy acid is prepared from benzaldehyde through the cyanohydrin, which is produced by interaction of the benzaldehyde bisulfite addition compound with potassium cyanide. This interchange reaction eliminates the hazard of working with volatile, toxic hydrogen cyanide, but even potassium cyanide is dangerous if safety measures are not observed. The interchange reaction is reversible and excess cyanide is used to shift the equilibrium in favor of the cyanohydrin. Mandelonitrile, a liquid, undergoes changes on standing and hence should be processed further without delay; it is extracted with ether, the solution is carefully washed free of cyanide ion, and the nitrile is then hydrolyzed with hydrochloric acid. An intermediate ketimine hydrochloride, C6H5CH(OH)C=NH*HCl soon gives way to mandelic acid and ammonium chloride, both of which are soluble in the aqueous acid. The solution is cooled and extracted with ether, and the ether is then displaced by benzene for crystallization, since mandelic acid is much less soluble in this solvent than in ether.

     

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