Cyanopelargonate

METHYL oi-CYANOPELARGONATE (Pelargonic acid, 0-cyano-, methyl ester) 

Tetrachloroethane is toxic the. operations should be conducted in a hood. 

In a 1.5-1. Erlenmeyer flask to which is attached a reflux condenser, 190 g. (0.88 mole) of methyl sebacamate (p. 71) is dissolved in 200 ml. of boiling tetrachloroethane. The solution is allowed to cool to 40-50° (Note 1), 95 g. (0.67 mole) of phosphorus pentoxide is added (Note 2), and the mixture is stirred well by means of a glass rod. The mixture is heated in an oil bath to 120° (thermometer in oil), and a second 95-g. portion of phosphorus pentoxide is added. After the mixture has been heated at 145° for 30 minutes with occasional hand stirring, the liquid is decanted. The residue is heated at 145° with 200 ml. of tetrachloroethane for 30 minutes with occasional stirring, and the liquid is decanted. This process is repeated once. The combined extracts are placed in a 1-1. flask, and most of the solvent is distilled under the reduced pressure of a water pump. The residue is transferred to a 300-ml. flask, and the remainder of the solvent is removed (Note 3). When no more distillate comes over, the receiver is changed, the water pump is replaced by an oil pump, and the residue is fractionated (Note 4). The yield 

The slush that results on cooling is easily mixed with the phosphorus pentoxide. 

The phosphorus pentoxide is weighed rapidly on a piece of paper, from which it can be slid quickly into the flask. 

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Methyl w-cyanopelargonate has also been prepared by esterification of w-cyanopelargonic acid with methyl sulfate 1 or methanol.2 The procedure described appears in the recent literature.1 3... 

SEBACONITRILE AND to-CYANOPELARGONIC ACID (Sebaconitrile and 0-cyanopelargonic acid)... 

An example is the preparation of sebaconitrile and oi-cyanopelargonic acid. A mixture of sebacic acid and urea is stirred and heated at 160° for 4 hrs., at which... 

Cyanononane, in M-00074 2-Cyanononanoic acid, C-00028 9-Cyanononanoic acid, C-00029 2-Cyanopelargonic acid, see C-00028 w-Cyanopelargonic acid, see C-00029 l-Cyano-2-propanol, in H-00232 1-Cyanopropene, in B-00040 Cycloartanol, C-00030 Cycloartenol, C-00031 Cycloartenone, in C-00031 1,12-Cyclodocosanedione, C-00032 Cycloeucalanol, in C-00033 Cycloeucalenol, C-00033 Cyclohexaneundecanoic acid, C-00034 Cyclohexylundecanoic acid, see C-00034 9/lJ,19-Cyclolanostan-3/5-ol, see C-00030 9/5,19-Cyclo-24-lanosten-3i5-ol, see C-00031 9/3,19-Cyclolanost-24-cn-3-one, in C-00031 Cyclolaudenol, in M-00022... 

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