Synthesis of hexanenitrile

Preparation of hexanenitrile

Alternative Names: Capronitrile; Tricapronile; Pentyl cyanide;

A mixture of 1 equiv. of hexanal and 1.1 equiv. of hydroxylamine hydrochloride are mixed with the dimethylsulfoxide until the homogeneous mixture is obtained (3-5 volumes) and the obtained mixture is stirred at 90° C for 1-2 hours. The reaction is monitored by TLC (ethyl acetate:hexane 5:95) and when is completed the mixture is cooled and poured in water,  the reaction product is extracted with ether, dried and the ether is removed by evaporation affording 95% of the hexanenitrile.

J. K. Augustine, et al. Synlett, 2223-2227, (2011) (supporting information)

IUPAC Name

hexanenitrile

InChI

InChI=1S/C6H11N/c1-2-3-4-5-6-7/h2-5H2,1H3

InChI Key

AILKHAQXUAOOFU-UHFFFAOYSA-N

Canonical SMILES

CCCCCC#N

Depositor-Supplied Synonyms

HEXANENITRILE, Capronitrile, Hexanonitrile, Tricapronile, n-Capronitrile, Pentyl cyanide, 1-Cyanopentane, 628-73-9, n-Amyl cyanide, NSC 1076, AILKHAQXUAOOFU-UHFFFAOYSA-N, EINECS 211-052-0, SBB060051, BRN 1633601, AI3-28396, 68002-67-5, Amyl Cyanide, n-Pentyl cyanide, n-Caproic nitrile, Nitriles, C6-12, (C6-C12)Alkylnitrile, AC1L1ZEO, ACMC-209n9n, WLN: NC5, 166650_ALDRICH, CTK2F3537, NSC1076, NSC-1076, EINECS 268-081-7, ANW-34425, ZINC01587817, AKOS000158157, AN-46913, KB-77743, LS-75141, TC-123170, TL8004299, FT-0623444, ST51046304, 4-02-00-00930 (Beilstein Handbook Reference), I14-106895, InChI=1/C6H11N/c1-2-3-4-5-6-7/h2-5H2,1H

Removed Synonyms

CID12352, H0102

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