Methyl iodide → Methyl 4-nitrobenzyl ether

Temperature

50 °C

A mixture of (4-nitro-phenyl)-methanol (3.0 g, 19.6 mmol), potassium carbonate (3.9 g, 28.1 mmol), acetonitrile (100 ml), and iodomethane (11 ml, 176 mmol) was heated at 50° C. for 48 hours. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium chloride solution (100 ml). The organic layer was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with hexane-dichloromethane (1:1 followed by 1:2) to yield 1-methoxymethyl-4-nitro-benzene (1.0 g, 31% yield).

1. concentrationThe mixture was concentrated under reduced pressure
2. customthe residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium chloride solution (100 ml)
3. concentrationThe organic layer was concentrated under reduced pressure
4. customThe residue was purified by flash chromatography on silica gel eluting with hexane-dichloromethane (1:1 followed by 1:2)

ORD record

ord-99a14f043af94ca4aecf75ea73d6e5ca

Source dataset

uspto-grants-2007_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07291616B2