Synthesis of capronitrile

Preparation of capronitrile

Preparation of capronitrile

Preparation of capronitrile

30 g of dry sodium cyanide (dried at 110º C overnight a) are mixed with 150 ml of dry dimethyl sulfoxide. The mixture is added to the flask fitted with a stirrer, reflux condenser, dropping funnel, and thermometer. The thick reaction slurry is heated to 90º C and the heating then  is stopped.  0.5 mole of 1-chloropentane  is slowly added to the stirred mixture causing the temperature to increase immediately. The rate of addition is such that the temperature of the reaction did not go above about 160º C. After all the 1-chloropentane is added the mixture is stirred for additional 10 min. more, or until the temperature dropped below 50º C. After the reaction is complete the mixture is poured into water and the product extracted several times with chloroform or ethyl ether. The extract is washed several times with saturated sodium chloride solution, dried over calcium chloride, and the capronitrile is distilled at 80° C/48mmHg yielding 97% of the final product.

J. Org. Chem., 1960, 25 (2), pp 257–258

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, ZINC1587817, EINECS 268-081-7, ANW-34425, ZINC01587817, AKOS000158157, AN-46913, KB-77743, LP105348, LS-75141, OR035532, 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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