Sodium Hydroxide → 4-(4-Fluorophenyl)-3-buten-2-one oxime

In a 250 ml single neck flask was charged 4.92 g (30 mmoles, 1.0 eq.) of 4-(4-fluorophenyl)-3-buten-2-one and 5.2 g (75.4 mmoles, 2.5 eq) of hydroxylamine hydrochloride and 6 g of 50% sodium hydroxide (75 mmoles, 2.5 eq) and 100 ml of methanol. The reaction mixture was stirred at reflux for 2 hours. The reaction mixture was concentrated, diluted with water (50 ml), and then extracted with ethyl acetate (2×50 ml). The organic phase was dried and concentrated, to obtain 3.4 of 4-(4-fluorophenyl)-3-buten-2one 2-oxime (E/Z mixture of isomers) as an oil in 63.3% yield.

1. temperatureat reflux for 2 hours
2. concentrationThe reaction mixture was concentrated
3. additiondiluted with water (50 ml)
4. extractionextracted with ethyl acetate (2×50 ml)
5. customThe organic phase was dried
6. concentrationconcentrated

ORD record

ord-cd370a17e7984fa382647226fdc39a4f

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06177462B1