Triethylamine → 2-Hydroxyimino-4-phenyl butyric acid ethyl ester

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Reaction Steps

103.14 g (0.5 mole) 2-oxo-4-phenyl butyric acid ethyl ester, 34.75 g (0.5 mole) hydroxylamine hydrochloride, 104 ml (0.75 mole) triethylamine and 500 ml ethanol were agitated overnight at room temperature. The batch was then evaporated to dryness and the residue taken up in 700 ml methyl-tert-butyl ether. After washing with 200 ml water, 200 ml 0.2N hydrochloric acid and 100 ml water, the organic phase was evaporated to dryness and the residue recrystallized after filtration from 170 ml toluene. 52.9 g (48%) 2-hydroxyimino-4-phenyl butyric acid ethyl ester were isolated in the form of colorless crystals. A 1H-NMR spectrum corroborated the suggested structure.

Provenance & Evidence