Acetaldehyde cyanohydrin

Acetaldehyde Cyanohydrin. This cyanohydrin, commonly known as lactonitnle, is soluble in water and alcohol, but insoluble in diethyl ether and carbon disulfide. Lactonitnle is used chiefly to manufacture lactic acid and its derivatives, primarily ethyl lactate. Lactonitnle [78-97-7] is manufactured from equimolar amounts of acetaldehyde and hydrogen cyanide containing 1.5% of 20% NaOH at —10 20 ° C. The product is stabili2ed with sulfuric acid (28). Sulfuric acid hydroly2es the nitrile to give a mixture of lactic acid [598-82-3] and ammonium bisulfate. 

The rate of reaction between hydrocyanic acid (HCN) and acetaldehyde (CH3CHO) to give acetaldehyde cyanohydrin has been studied in a constant-volume batch reactor at 25°C in dilute aqueous solution, buffered to keep the pH constant (Svirbely and Roth, 1953). The reaction is... 

The nitrile group is very sensitive to alkalis and the elimination of it by the action of potassium hydroxide on acetaldehyde cyanohydrin was described by Simpson and Gauthier as one of the reactions of the acetaldehyde cyanohydrin, a substance that they prepared for the first time. That the nitriles of the aldonic acids yield cyanides under the action of alkali, is described by Wohl as one of the properties of penta-acetyl-D-glucononitrile. 

Two methods of prepn are listed in Ref 3 a)By esterification of lactic acid with ethanol and b)By combining acetaldehyde with hydrocyanic. acid to form acetaldehyde cyanohydrin, and this is treated wi th ethanol HC1 to ethyl lactate. Used as a solvent for cellulose acetate and nitrate, other cellulose esters, resins, lacquers, paints and enamels Refs l)Beil 3, 264, 267, 280,(102,109) ... 

Michael addition to a complexed styrene. A key step in a synthesis of 11-deoxy-anthracyclinone (3) involves the regioselective reaction of 1 with the carbanion of a protected acetaldehyde cyanohydrin to give 2 by stereospecific earo-addition. 

Derivation (a) By the esterification of lactic acid with ethanol (b) by combining acetaldehyde with hydrogen cyanide to form acetaldehyde cyanohydrin, which is converted into ethyl lactate by treatment with ethanol and an inorganic acid. 

Beilstein Handbook Reference) Acetaldehyde, cyanohydrin Acetocyanohydrin AI3-24276 BRN 0605366 CCRIS 6048 EINECS 201-163-2 EINECS 265-852-8 Ethylidene cyanohydrin HSDB 5225 Lactonitrile Laktonitril NSC 7764 Propanenitrile, 2-hydroxy- Propionitrile, 2-hydroxy-. Used as a solvent and an intermediate in production of ethyl lactate and lactic acid. Liquid mp = -40° bp = 183° d ° = 0,9877 freely soluble in H2O, organic solvents LDso (mrat orl) = 31 mg/kg (frat orl) = 41 mgfkg LCLo (rat ihl) = 124 ppm, 4 hr. Lancaster Synthesis Co.,-Mallinckrodt Inc. Sigma-Akirich Fine Chem. Supernutrition. 

Ethyl cyanoacetate is converted by acetaldehyde cyanohydrin in the presence of sodium alkoxide into ethyl 2,3-dicyanobutyrate in 80% yield.670... 

See Benzyl methoxyethyl acetal Acetaldehyde cyanohydrin. See Lactonitrile Acetaldehyde diethyl acetal. See Acetal Acetaldehyde dihexylacetal CAS 5405-58-3... 

Synonyms Acetaldehyde cyanohydrin 2-Hydroxypropionitrile a-Hydroxypropionitrile Propionitrile, 2-hydroxy-... 

An interesting variant of these Michael-type additions is the 1,6-addition of the anion of type (29) to a dienyl sulfone as a route to tagetones and 1,4-addition to nitrostyrene to form 3-nitro ketones. A key step in a synthesis of 11-deoxyanthracyclinone involves die regioselective reaction of complexed stjmne with lithiated protected acetaldehyde cyanohydrin. ... 

For example, HCN adds to acetaldehyde to form acetaldehyde cyanohydrin in to the same carbon. 

The value of cyanohydrins as synthetic intermediates lies in the new functional groups into which they can be converted. First, the secondary or tertiary hydroxyl group of the cyanohydrin may undergo acid-catalyzed dehydration to form an unsaturated nitrile. For example, acid-catalyzed dehydration of acetaldehyde cyanohydrin gives acrylonitrile, the monomer from which polyacrylonitrile (Orion, Table 29.1) is made. 

Acetaldehyde cyanohydrin 6181 Adriamycin hydrochloride 4666 4-Amino-4 -chlorodiphenyl 1919... 

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