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Glycolonitrile is produced by reacting formaldehyde with hydrogen cyanide at near-neutral pH, but with small amounts of catalytic base. [5] Glycolonitrile polymerizes under alkaline conditions above pH 7.0. As the product of polymerization is an amine with a basic character, the reaction is self-catalysed, gaining in speed with ongoing conversion.
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:
Cyanohydrins are sources of highly toxic hydrogen cyanide.The substance is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.
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 ...
In transhydrocyanation, an equivalent of HCN is transferred from a cyanohydrin, e.g. acetone cyanohydrin, to another HCN acceptor. The transfer is an equilibrium process, initiated by base. The reaction can be driven by trapping reactions or by the use of a superior HCN acceptor, such as an aldehyde. [6]
(CH 3) 3 SiCN + H 2 O → (CH 3) 3 SiOH + HCN. In its principal application, it adds across carbon-oxygen double bonds, for example in an aldehyde, to form a new carbon-carbon bond: [2] RCH=O + (CH 3) 3 SiC≡N → N≡C– CHR–O Si(CH 3) 3. The product is an O-silylated cyanohydrin. One use of this reagent is to convert pyridine-N-oxides ...
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
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 ...
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