Hydrochloric Acid → 1-(3-Methoxy-4-nitrophenyl)ethan-1-one

A suspension of MgCl2 (932 mg, 9.8 mmol) in toluene (13 mL) was treated with triethylamine (4.65 mL, 33.4 mmol), dimethyl malonate (1.9 mL, 16.6 mmol), stirred for 1.5 hours, and treated portionwise over 30 minutes with 3-methoxy-4-nitrobenzoyl chloride (3 g, 13.9 mmol). The reaction mixture was stirred for 45 minutes, then carefully treated with concentrated HCl (4 mL). The layers were separated and the organic phase was dried (Na2SO4), filtered, and concentrated. The, residue was dissolved in DMSO (11.5 mL) and water (0.5 mL), heated to reflux overnight, cooled to room temperature, and partitioned between water and ethyl acetate. The organic phase was washed sequentially with saturated NaHCO3, water, and brine, dried (MgSO4), filtered, and concentrated to provide 1.63 g (60% yield) of the desired product. MS (ESI(−)) m/e 194 (M−H)−.

1. stirringThe reaction mixture was stirred for 45 minutes
2. customThe layers were separated
3. dry with materialthe organic phase was dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe, residue was dissolved in DMSO (11.5 mL)
7. temperaturewater (0.5 mL), heated
8. temperatureto reflux overnight
9. custompartitioned between water and ethyl acetate
10. washThe organic phase was washed sequentially with saturated NaHCO3, water, and brine
11. dry with materialdried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated

ORD record

ord-7059b005a5224231a345b152e16158c9

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560552B2