Isobutyraldehyde → 4-Formyl-4-methylvaleronitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 64.8 g (0.898 mmol, 51.45 mL) of isobutyraldehyde in 300 mL of dry dioxane was added 300 mg of hydroquinone (0.0027 mmol) and 60.0 g (1.13 mmol; 1.26 eq; 48.4 mL) of acrylonitrile. To this stirred solution was added all at once a freshly prepared solution of 3 g of NaOH dissolved in 60 mL of water and the whole was heated at 65° C. during 150 min. After cooling to 20° C., removal of the solvents under aspirator vacuum gave a residue which was partitioned between water and CH2Cl2. After separation, the aqueous layer was extracted 3 times with CH2Cl2 and the combined organic layers dried over Na2SO4 and concentrated under vacuum (aspirator). The crude residue was distilled under vacuum (81° C./1 mm Hg) to yield 54 g (49%) of 4,4-dimethyl-5-oxovaleronitrile.

Provenance & Evidence