Isobutyraldehyde → 4-Formyl-4-methylvaleronitrile

Temperature

65 °C

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./lmm Hg) to yield 54 g (49%) of 4,4-dimethyl-5-oxovaleronitrile.

1. temperatureAfter cooling to 20° C.
2. customremoval of the solvents under aspirator vacuum
3. customgave a residue which
4. customwas partitioned between water and CH2Cl2
5. customAfter separation
6. extractionthe aqueous layer was extracted 3 times with CH2Cl2
7. dry with materialthe combined organic layers dried over Na2SO4
8. concentrationconcentrated under vacuum (aspirator)
9. distillationThe crude residue was distilled under vacuum 81° C./lmm Hg)

ORD record

ord-02ef0ce0bcf74f7cac08b6310ab9ccdf

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04841045