Chloromethyl Methyl Ether → 3-Chloro-4-[2-(methoxy-methoxy)ethyl]aniline

To a stirred solution of 2-(2-chloro-4-nitrophenyl)ethanol (2.9 g) in dichloromethane (20 ml) were added N,N-diisopropyl-ethylamine (3.0 ml) and chloromethyl methyl ether (1.2 ml) under ice-cooling, and the mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (20 ml), 3% platinum sulfide on activated carbon (wet) (842 mg) was added, and the mixture was stirred for 10 hours under a hydrogen atmosphere. After the catalyst was removed by filtration, the solvent was removed under reduced pressure to give 3-chloro-4-[2-(methoxy-methoxy)ethyl]aniline (2.0 g).

1. temperaturecooling
2. extractionextracted with ethyl acetate
3. washThe extract was washed with brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was removed under reduced pressure
6. dissolutionThe residue was dissolved in methanol (20 ml)
7. addition3% platinum sulfide on activated carbon (wet) (842 mg) was added
8. stirringthe mixture was stirred for 10 hours under a hydrogen atmosphere
9. customAfter the catalyst was removed by filtration
10. customthe solvent was removed under reduced pressure

ORD record

ord-66f4af141e7b416ab093a7869a1c8737

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06696489B1