ChemicalBook CAS DataBase List Trimethylacetonitrile

Trimethylacetonitrile synthesis

12synthesis methods

Product Name:Trimethylacetonitrile
CAS Number:630-18-2
Molecular formula:C5H9N
Molecular Weight:83.13

630-19-3 Synthesis

630-19-3
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$13.00/1g

630-18-2
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$10.00/1g

Yield:630-18-2 64 %Chromat.

Reaction Conditions:

with ammonium acetate;acetic acid;4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate at 70; for 12 h;Inert atmosphere;

Steps:

General procedures for 4-AcNH-TEMPO⁺BF₄^- mediated nitriles synthesis
General procedure: A 15 mm flame-dried test tube, which was equipped with a magnetic stir bar and charged with aldehyde (0.3 mmol, in case of solid), 4-AcNH-TEMPO⁺BF₄^- (2.0 equiv, 0.6 mmol), and NH₄OAc (4.0 equiv, 1.2 mmol), was evacuated and backfilled with nitrogen (this process was repeated 3 times). After 0.3 mL of AcOH was added, aldehyde (0.3 mmol, in case of liquid), and AcOH (0.3 mL) were added in sequence. The reaction mixture was stirred for 12 h at 70 ^oC under N₂ balloon, and then cooled to room temperature. The reaction was diluted by adding EtOAc and washed 4 M HCl aqueous solution. Two layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with Na₂CO₃ aqueous solution. The organic layer was dried over MgSO_4,filtered, and concentrated to a volume of approximately 20 mL by evaporator. To eliminate remaining aldehyde, aqueous 2 M Na₂S₂O₅ aqueous solution (20 mL) was added to the organic layer and stirred for 2 hours.Two layers were separated, and the organic layer was dried over MgSO_4,filtered, and concentrated in vacuo. The residue was purified by column chromatography to give nitrile products.