Sodium Hydroxide → N-[4-(2-Chlorophenyl)but-3-en-2-ylidene]hydroxylamine

In a 250 ml single neck flask was charged 5.4 g (29.9 mmoles, 1.0 eq.) of (E)-4-(2-chlorophenyl)-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 g of 4-(2-chlorophenyl)-3-buten-2-one 2-oxime (E/Z mixture of oximes) as an oil in 58.1% 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-35a581b6cbf04810b891f5c7c4c14275

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06177462B1