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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 ]
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:
In organic chemistry, a cyanohydrin reaction is an organic reaction in which an aldehyde (−CH=O) or ketone (>C=O) reacts with a cyanide anion (N≡C −) or a nitrile (−C≡N) to form a cyanohydrin (>C(OH)C≡N). For example:
Another synthetic pathway for α-hydroxy acids involves the addition of hydrogen cyanide to ketones or aldehydes, followed by the acidic hydrolysis of the cyanohydrin intermediate. [14] R−CHO + HCN → R−CH(OH)CN R−CH(OH)CN + 2H 2 O → R−CH(OH)CO 2 H + NH 3
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 ...
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
Chloral cyanohydrin is the cyanohydrin derivative of chloral (trichloroacetaldehyde). It was historically used as a source of hydrogen cyanide for medicinal purposes. [ 1 ] Chloral cyanohydrin is toxic by inhalation.
It is commonly collected as a byproduct of the "acetone cyanohydrin route" to the commodity chemical methyl methacrylate. [1] It can also be obtained by hydrolysis of sulfamic acid in aqueous solution, which produces the salt in high purity: H 3 NSO 3 + H 2 O → (NH 4)HSO 4. It also arises by the thermal decomposition of ammonium sulfate:
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