Synthesis of mandelonitrile (Benzaldehyde cyanohydrin)

Preparation of mandelonitrile

Preparation of mandelonitrile

Preparation of mandelonitrile

15 g of benzaldehyde is thoroughly stirred for one-half hour, with 50 ml (excess) of concentrated sodium bisulfite solution. The crystalline bisulfite addition product – sodium hydroxy(phenyl)methanesulfonate, is filtered off, washed with alcohol, and stirred to a thin paste with water. A 30% solution of 12 g (excess) of potassium cyanide (or sodium cyanide) is then added all at once, with vigorous stirring. The sodium hydroxy(phenyl)methanesulfonate quickly dissolves, and the oily mandelonitrile, precipitates in almost quantitative yield. The crystals of mandelonitrile are separated from the solution by filtration and dried in vacuum.

An advanced laboratory manual of organic chemistry, M. Heidelberger, 48-49, 1923

Preparation of benzaldehyde cyanohydrin

Preparation of benzaldehyde cyanohydrin

14 g of finely powdered 96% potassium cyanide, and 20 g of freshly distilled benzaldehyde are placed in a flask cooled with ice and salt. Conc. hydrochloric acid, corresponding to 7 g of anhydrous acid (about 20 g conc. acid will be required), are slowly dropped in with frequent shaking. The whole is allowed to stand for 1 hour, being shaken at frequent intervals; it is then poured into 5 volumes of water, and the oil which separates well washed with water several times; a further purification is impossible owing to its instability. Yield 26 g (theoretical).

Systematic organic chemistry, by W. M. Cumming, 156, 1937.

IUPAC Name

2-hydroxy-2-phenylacetonitrile

InChI

InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H

InChI Key

NNICRUQPODTGRU-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)C(C#N)O

MeSH Synonyms

mandelonitrile, mandelonitrile, (+-)-isomer

Depositor-Supplied Synonyms

Mandelonitrile, Mandelic acid nitrile, Benzaldehyde cyanohydrin, Phenylglycolonitrile, Amygdalonitrile, hydroxy(phenyl)acetonitrile, Glycolonitrile, phenyl-, ALPHA-HYDROXYBENZENEACETONITRILE, 532-28-5, Benzaldehydkyanhydrin, Acetonitrile, hydroxyphenyl-, Nitril kyseliny mandlove, Benzaldehyde, cyanohydrin, Benzeneacetonitrile, .alpha.-hydroxy-, alpha-Hydroxyphenylacetonitrile, 2-hydroxy-2-phenylacetonitrile, DL-MANDELONITRILE, Mandelonitrile, (+-)-, NSC 77668, Benzaldehydkyanhydrin [Czech], CCRIS 4656, 2-hydroxy-2-phenyl-acetonitrile, CHEBI:16910, Nitril kyseliny mandlove [Czech], .alpha.-Hydroxybenzeneacetonitrile, NNICRUQPODTGRU-UHFFFAOYSA-N, Benzeneacetonitrile, alpha-hydroxy-, EINECS 208-532-7, (+-)-alpha-Hydroxybenzeneacetonitrile, BRN 2207122, AI3-50437, ST51037901, 613-88-7, AC1L1VVW, AC1Q4QUM, WLN: QYR&CN, DSSTox_CID_5422, (.+/-.)-Mandelonitrile, hydroxyl(phenyl)acetonitrile, .alpha.-Cyanobenzyl alcohol, DSSTox_RID_77778, NCIOpen2_000888, DSSTox_GSID_25422, SCHEMBL196731, 116025_ALDRICH, AC1Q76I7, 2-hydroxy-2-phenylethanenitrile, 2-hydroxyl-2-phenylacetonitrile, CHEMBL1393845, 12023_FLUKA, CTK8G4054, MolPort-001-779-743, Hydroxyphenylacetonitrile (Related), NSC77668, Tox21_200804, LS-193, NSC-77668, STL164354, AKOS005363772, NCGC00090867-01, NCGC00090867-02, NCGC00258358-01, AN-45637, CAS-532-28-5, FT-0083190, FT-0622621, M0566, mandelonitrile,( inverted exclamation markA)-, 4-10-00-00578 (Beilstein Handbook Reference), I14-62525, 3B3-033177, 3B3-070235

Removed Synonyms

|A-hydroxybenzeneacetonitrile, CID10758

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