Isobutyraldehyde → 4-Formyl-4-methylvaleronitrile

Participants

Reaction Conditions

Reaction Steps

Isobutyraldehyde (12.7 mL, 138.6 mmol), a catalytic amount of hydroquinone (50 mg) and acrylonitrile (9.2 g, 173.4 mmol) were dissolved in 1,4-dioxane (50 mL), and 5% NaOH solution (9.2 mL) was added. The reaction was heated at 65° C. for 2.5 h and then stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure, and the organic product was extracted with CH2Cl2. The combined extracts were washed with H2O and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 15-20% EtOAc in petroleum ether) to afford 4,4-dimethyl-5-oxopentanenitrile (11.0 g, yield 63%). 1H NMR (400 MHz, CDCl3) δ 9.45 (s, 1H), 2.34-2.30 (m, 2H), 1.93-1.89 (m, 2H), 1.14 (s, 6H)

Provenance & Evidence