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In the laboratory, this liquid serves as a source of HCN, which is inconveniently volatile. [4] Thus, acetone cyanohydrin can be used for the preparation of other cyanohydrins, for the transformation of HCN to Michael acceptors, and for the formylation of arenes. Treatment of this cyanohydrin with lithium hydride affords anhydrous lithium cyanide:
The chemist Urech in 1872 was the first to synthesize cyanohydrins from ketones with alkali cyanides and acetic acid [2] and therefore this reaction also goes by the name of Urech cyanohydrin method. References
It is used as a surrogate in place of HCN, as illustrated by its use as a precursor to lithium cyanide: [8] (CH 3) 2 C(OH)CN + LiH → (CH 3) 2 CO + LiCN + H 2. In transhydrocyanation, an equivalent of HCN is transferred from acetone cyanohydrin to another acceptor, with acetone as byproduct. The transfer is an equilibrium process, initiated by ...
Glycolonitrile, also called hydroxyacetonitrile or formaldehyde cyanohydrin, is the organic compound with the formula HOCH 2 CN. It is the simplest cyanohydrin and it is derived from formaldehyde . [ 3 ]
LiCN is produced from the reaction of lithium hydroxide and hydrogen cyanide. A laboratory-scale preparation uses acetone cyanohydrin as a surrogate for HCN: [5] (CH 3) 2 C(OH)CN + LiH → (CH 3) 2 CO + LiCN + H 2
Linamarin is a cyanogenic glucoside found in the leaves and roots of plants such as cassava, lima beans, and flax.It is a glucoside of acetone cyanohydrin.Upon exposure to enzymes and gut flora in the human intestine, linamarin and its methylated relative lotaustralin can decompose to the toxic chemical hydrogen cyanide; hence food uses of plants that contain significant quantities of ...
Large-scale applications are for the production of potassium cyanide and adiponitrile, used in mining and plastics, respectively. [10] It is more toxic than solid cyanide compounds due to its volatile nature. A solution of hydrogen cyanide in water, represented as HCN, is called hydrocyanic acid. The salts of the cyanide anion are known as ...
This transformation is best done in dichloromethane solution using dimethylcarbamoyl chloride as the activating electrophile. It is possible to use benzoyl chloride but the yields and regioselectivity of the addition of the cyano group are lower. Acetone cyanohydrin can be used to reversibly generate the cyanide anion. [5] (4)