Synthesis of benzyl cyanide (phenylacetonitrile)

Preparation of benzyl cyanide

Preparation of benzyl cyanide (phenylacetonitrile)

Preparation of benzyl cyanide (phenylacetonitrile)

30 g of pure potassium cyanide are dissolved in 25 ml of water and the solution is added in a 500 ml round flask attached to a reflux condenser. Heat is applied and to this hot solution slowly 50 g of benzyl chloride dissolved in an equal weight of alcohol are added. The reaction mixture is refluxed gently 3-4 hours. The liquid separates into two layers; the upper brown layer consisting of an alcoholic solution of benzyl cyanide and the lower of an aqueous solution of potassium chloride. The upper layer is separated and fractionally distilled. Alcohol first distills, a little water follows and, when the temperature reaches 210° C, the distillate consists of benzyl cyanide. The fraction passing between 210° C and 235° C is collected. The yield of benzyl cyanide is about 35 g.

A Class-Book of Organic Chemistry, by J. B. Cohen, 4-5, 1919

IUPAC Name

2-phenylacetonitrile

InChI

InChI=1S/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H2

InChI Key

SUSQOBVLVYHIEX-UHFFFAOYSA-N

Canonical SMILES

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

MeSH Synonyms

benzyl cyanide, phenylacetonitrile

Depositor-Supplied Synonyms

Phenylacetonitrile, Benzeneacetonitrile, BENZYL CYANIDE, 2-Phenylacetonitrile, 140-29-4, alpha-Tolunitrile, Benzyl nitrile, alpha-Cyanotoluene, (Cyanomethyl)benzene, Phenyl acetyl nitrile, Acetonitrile, phenyl-, 2-phenylethanenitrile, USAF KF-21, benzylcyanide, Benzylnitrile, Phenyl-acetonitrile, .alpha.-Tolunitrile, .alpha.-Cyanotoluene, .omega.-Cyanotoluene, Benzylkyanid [Czech], Toluene, alpha-cyano-, Phenylacetonitrile, liquid, Toluene, .alpha.-cyano-, NSC 118418, Acetic acid, phenyl-nitrile, UNII-23G40PRP93, CCRIS 4698, HSDB 2103, SUSQOBVLVYHIEX-UHFFFAOYSA-N, EINECS 205-410-5, SBB058386, UN2470, AI3-04975, WLN: NC1R, Benzylkyanid, benzyl-cyanide, Phenacetonitrile, omega-Cyanotoluene, benzene acetonitrile, benzene-acetonitrile, 2-phenyl-acetonitrile, A-TOLUNITRILE, alpha-phenylacetonitrile, PubChem20468, AC1L1RPP, ACMC-1C0PN, DSSTox_CID_1492, AC1Q4S1D, C8H7N, DSSTox_RID_76184, DSSTox_GSID_21492, SCHEMBL37831, B19401_ALDRICH, KSC175C3P, 13300_FLUKA, CHEBI:25979, CTK0H5137, NSC3407, MolPort-001-768-890, OTAVA-BB 1519434, 23G40PRP93, NSC-3407, Tox21_200217, ANW-20559, LABOTEST-BB LT00891699, LS-817, NSC118418, ZINC01666748, AKOS000118943, AS01366, MCULE-3500109780, NSC-118418, RP19286, RTC-061401, UN 2470, NCGC00090854-01, NCGC00090854-02, NCGC00257771-01, AN-23174, CAS-140-29-4, CJ-26987, KB-47802, SC-26879, DB-004016, FT-0636686, FT-0657342, P0128, ST51017243, C16074, Phenylacetonitrile, liquid [UN2470] [Poison], Phenylacetonitrile, liquid [UN2470] [Poison], A807640, 3B4-1076, S01-0547, InChI=1/C8H7N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6H

Removed Synonyms

|tolunitrile, phenyl acetonitrile, CID8794, c0647

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