Ethanol → 4-Isobutylbenzaldehyde oxime

To a solution of 4-isobutylbenzaldehyde (5.0 g, 31 mmol) in a mixed solvent of ethanol (25 ml) and pyridine (25 ml) was added hydroxylamine hydrochloride (2.4 g, 34 mmol) with stirring, and the resulting mixture was stirred at room temperature for 18 hours. After evaporating the reaction mixture in vacuo, the residue thus obtained was diluted with ether, poured into water (150 ml) and extracted with ether. The extract was washed successively with 1N hydrochloric acid and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:19 to 1:9) as the eluent to afford the title compound (4.6 g) in a yield of 84% as a colourless oily product.

1. stirringthe resulting mixture was stirred at room temperature for 18 hours
2. customAfter evaporating the reaction mixture in vacuo
3. customthe residue thus obtained
4. extractionextracted with ether
5. washThe extract was washed successively with 1N hydrochloric acid
6. dry with materiala saturated aqueous solution of sodium chloride and dried over magnesium sulfate
7. filtrationAfter filtration
8. customthe filtrate was evaporated in vacuo

ORD record

ord-d46253ce467a462ebd250c6065799f66

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2