ChemicalBook CAS DataBase List OCTANENITRILE

OCTANENITRILE synthesis

13synthesis methods

Product Name:OCTANENITRILE
CAS Number:124-12-9
Molecular formula:C8H15N
Molecular Weight:125.21

5458-59-3
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$36.00/25mL

124-12-9
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$21.00/5mL

Yield:124-12-9 82%

Reaction Conditions:

Stage #1:1-methylethyl octanoate with diisobutylaluminium hydride in hexane;dichloromethane at -78 - -60; for 2 h;Inert atmosphere;
Stage #2: with ammonia;iodine in tetrahydrofuran;hexane;dichloromethane;water at -60 - 20;Inert atmosphere;

Steps:

4.3. Typical procedure for the conversion of isopropyl esters (3) into nitriles (4)
General procedure: To a solution of isopropyl tetradecanoate (555 mg, 2.05 mmol) in CH₂Cl₂ (2 mL) was added DIBAL-H (1.04 M in hexane, 3 mL, 1.5 equiv) at -78 °C. The mixture was stirred for 3 h at -78 °C under argon atmosphere. Then, aq NH₃ (6 mL), THF (3 mL), and I₂ (1.85 mg, 7.30 mmol) were added. The resulting solution was warmed to room temperature and stirred for 3 h. Reaction mixture was poured into saturated aq Na₂SO₃ solution (10 mL) and extracted with chloroform (15 mL×3). The organic layer was dried over Na₂SO₄. After removal of the solvent under reduced pressure, the residue was purified by short column chromatography on silica gel to give tetradecanenitrile in 90% (386 mg).

References:

Suzuki, Yusuke;Yoshino, Takumi;Moriyama, Katsuhiko;Togo, Hideo [Tetrahedron,2011,vol. 67,# 21,p. 3809 - 3814] Location in patent:experimental part