Methane, dichloromethoxy- → N-(1-(4-formylphenyl)ethyl)acetamide

Temperature

25 °C

To a solution of N-(1-phenylethyl)acetamide (5.0 g) in dichloromethane (100 ml) was added dropwise titanium tetrachloride (16.7 ml) at below 5° C. over 30 min. Thereto was added dropwise a solution of dichloromethyl methyl ether (14.1 ml) in dichloromethane (30 ml) solution at below 5° C. over 30 min. The mixture was stirred at 25° C. for 3 hr, at room temperature for 12 hr, and then at 25° C. for 3 hr, and poured into ice water (800 ml) and extracted with ethyl acetate. The extract was washed successively with a saturated sodium hydrogencarbonate solution (500 ml) and saturated brine (500 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=1:3) to give the title compound (0.35 g) as a colorless oil.

1. waitat 25° C. for 3 hr
2. extractionextracted with ethyl acetate
3. washThe extract was washed successively with a saturated sodium hydrogencarbonate solution (500 ml) and saturated brine (500 ml)
4. dry with materialdried over anhydrous sodium sulfate
5. customThe solvent was evaporated
6. customthe obtained residue was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=1:3)

ORD record

ord-d4ee8417fec840e682cbc0058e03d458

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455528B1