Pyridine → 1-hydroxy-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime

Temperature

24 °C

To a stirred solution of 1-hydroxy-3-(2,4,6-trichloro-phenyl)-propan-2-one (30 g; 118 mmol) in methanol (240 ml) was added pyridine (15 ml; 189 mmol) followed by a portionwise addition of methoxyamine hydrochloride (15 g; 178 mmol). The reaction mixture was stirred at 24° C. for 18 h under nitrogen. Methanol was removed under reduced pressure, the residue poured in water (300 ml) and 1N hydrochloric acid was added (100 ml). The solution was extracted with dichloromethane (3×150 ml). Combined organic layers were washed with water (300 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford 33 g (99% of theory) of 1-hydroxy-3-(2,4,6-trichloro-phenyl)-propan-2-one O-methyl-oxime (isomers E/Z 1:1) as a brown oil.

1. customMethanol was removed under reduced pressure
2. additionthe residue poured in water (300 ml)
3. addition1N hydrochloric acid was added (100 ml)
4. extractionThe solution was extracted with dichloromethane (3×150 ml)
5. washCombined organic layers were washed with water (300 ml)
6. dry with materialdried over sodium sulfate
7. customThe solvent was removed in vacuo

ORD record

ord-6beada7a976d44e2bd4908ced01bfb30

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552049B2