4-Chlorobenzaldehyde → 4-Chloro-benzaldehyde oxime

To a solution of 4-chlorobenzaldehyde (10.0 g) in chloroform (350 mL), hydroxylamine hydrochloride (10.2 g) was added and the mixture was stirred at room temperature for 18 hours in an argon atmosphere. After adding 2 mol/L hydrochloric acid (200 mL), three extractions were conducted with chloroform. The combined organic layers were washed with saturated brine and thereafter dried over anhydrous magnesium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was crystallized with a liquid mixture of n-hexane and chloroform to give 1-(4-chlorophenyl)-N-hydroxymethaneimine as a colorless solid (9.27 g).

1. additionAfter adding
2. extraction2 mol/L hydrochloric acid (200 mL), three extractions
3. washThe combined organic layers were washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customAfter removing the
6. filtrationdesiccant by filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe resulting residue was crystallized with a liquid mixture of n-hexane and chloroform

ORD record

ord-d46ebc14062a4c30a3c57ea3e5038850

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422240B2