Synthesis of undecanenitrile

Preparation of undecanenitrile

Preparation of undecanenitrile

Preparation of undecanenitrile

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-chlorodecane 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-chlorodecane 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 undecanenitrile is distilled at 129°C/11mmHg yielding 94% of the final product.

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

IUPAC Name

undecanenitrile

InChI

InChI=1S/C11H21N/c1-2-3-4-5-6-7-8-9-10-11-12/h2-10H2,1H3

InChI Key

SZKKNEOUHLFYNA-UHFFFAOYSA-N

Canonical SMILES

CCCCCCCCCCC#N

Depositor-Supplied Synonyms

UNDECANENITRILE, Undecanonitrile, 2244-07-7, 1-Cyanodecane, n-Decyl cyanide, SZKKNEOUHLFYNA-UHFFFAOYSA-N, SBB060054, Decyl Cyanide, Undecanoic acid nitrile, ACMC-1CKN8, AC1L28JR, SCHEMBL61880, CTK1A6976, NSC4026, NSC 4026, NSC-4026, ZINC1672957, EINECS 218-826-7, 5901AF, ANW-13712, AKOS009159057, MCULE-7957242645, LP004541, AI3-28302, DB-055501, TC-102456, ST50411983, U0044, I14-18631, I14-106657

Removed Synonyms

Dodecanenitrile, C11H21N, CID16722, 2437-25-4, 71172-36-6

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