Synthesis of acetone cyanohydrin

Preparation of acetone cyanohydrin (2-hydroxy-2-methylpropanenitrile; 2-hydroxyisobutyronitrile; alpha-hydroxyisobutyronitrile)

Preparation of acetone cyanohydrin (2-hydroxy-2-methylpropanenitrile; 2-hydroxyisobutyronitrile; alpha-hydroxyisobutyronitrile)

Preparation of acetone cyanohydrin (2-hydroxy-2-methylpropanenitrile; 2-hydroxyisobutyronitrile; alpha-hydroxyisobutyronitrile)

A 1-litre three-necked flask is fitted with a mechanical stirrer, a dropping funnel, and a thermometer. A solution of 47 g of sodium cyanide (or 62 g of potassium cyanide) dissolved in 200 ml of water is placed in the flask with 73.5 ml (58 g) of pure acetone. From the dropping funnel, with constant stirring, 275 ml (334 g) of 30% sulfuric acid are slowly dropwise added. The temperature during the addition should not rise above 15-20° C. If necessary, a crushed ice is added to the mixture. After all the sulfuric acid has been added the stirring is continued for 15 minutes. The obtained reaction product is extracted with three 50 ml portions of ether, the ethereal extracts are dried with anhydrous sodium or magnesium sulfate, the ether is removed by evaporation and the residue is purified by distillation under diminished pressure. The fraction passing at 80-82°/15 mm is collected yielding 62 g of pure  acetone cyanohydrin.

Org. Synth. 1935, 15, 1

A text book of practical organic chemistry, by A. I. Vogel, 348, 1974

IUPAC Name

2-hydroxy-2-methylpropanenitrile

InChI

InChI=1S/C4H7NO/c1-4(2,6)3-5/h6H,1-2H3

InChI Key

MWFMGBPGAXYFAR-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C#N)O

MeSH Synonyms

acetoncyanhydrine, acetone cyanohydrin, acetone cyanohydrin, 14C-labeled

Depositor-Supplied Synonyms

ACETONE CYANOHYDRIN, 2-Hydroxy-2-methylpropanenitrile, 2-Hydroxyisobutyronitrile, 2-Methyllactonitrile, Acetone cyanhydrin, alpha-Hydroxyisobutyronitrile, 75-86-5, 2-Cyano-2-propanol, Acetoncianidrina, Acetoncyanhydrin, Acetonkyanhydrin, Acetoncianhidrinei, Acetoncyaanhydrine, Acetonecyanhydrine, Propanenitrile, 2-hydroxy-2-methyl-, 2-Propanone, cyanohydrin, Lactonitrile, 2-methyl-, 2-Cyano-2-hydroxypropane, USAF RH-8, Cyanhydrine d’acetone, 2-Hydroxy-2-methylpropionitrile, RCRA waste number P069, .alpha.-Hydroxyisobutyronitrile, Acetonkyanhydrin [Czech], Acetoncyanhydrin [German], Acetoncianidrina [Italian], Acetoncyaanhydrine [Dutch], RCRA waste no. P069, Acetonecyanhydrine [French], NSC 131093, Acetoncianhidrinei [Romanian], Acetone cyanohydrin, stabilized, CCRIS 4657, HSDB 971, Cyanhydrine d’acetone [French], CHEBI:15348, 2-hydroxy-2-methyl-propionitrile, 2-hydroxy-2-methyl-propanenitrile, MWFMGBPGAXYFAR-UHFFFAOYSA-N, EINECS 200-909-4, UN1541, BRN 0605391, AI3-04257, DSSTox_CID_5427, DSSTox_RID_77782, DSSTox_GSID_25427, WLN: QX1&1&CN, CAS-75-86-5, 59182-86-4, CNH, Acetonecyanohydrin, acetone cyano-hydrin, 2-Cyanopropan-2-ol, PubChem22297, CO1YOV1KFI, UNII-CO1YOV1KFI, AC1L1MGL, AC1Q1NNM, A10000_ALDRICH, NSC977, 2-methyl-2-hydroxypropionitrile, CHEMBL1231861, DIMETHYLKETONE CYANOHYDRIN, 00591_FLUKA, NSC-977, NSC7080, 2-hydroxy-2-methylpropane nitrile, MolPort-000-871-976, BB_SC-6536, 2-methyl-2-oxidanyl-propanenitrile, 2-Hydroxy-2-methylpropanenitrile #, NSC-7080, Tox21_201490, Tox21_303256, BBL011349, NSC131093, SBB004397, STL146439, AKOS000118890, DB02203, LS-1677, MCULE-7494613383, NSC-131093, UN 1541, NCGC00249054-01, NCGC00257016-01, NCGC00259041-01, AN-42023, KB-173606, FT-0083168, FT-0621802, M0361, C02659, 4-03-00-00785 (Beilstein Handbook Reference), A838531, 3B4-3598, Acetone cyanohydrin, stabilized [UN1541] [Poison], S14-0985, T7028075, Acetone cyanohydrin, stabilized [UN1541] [Poison], InChI=1/C4H7NO/c1-4(2,6)3-5/h6H,1-2H

Removed Synonyms

acetoncyanhydrine, acetone cyanohydrin, 14C-labeled, CID6406, C010833

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