Hydrochloric Acid → Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester

To a solution of 4-methoxybenzoic acid (26.2 g, 172 mmol) in tetrahydrofuran (150 ml) was added 1,1′-carbonylbis-1H-imidazole (30.7 g, 189 mmol) and the mixture was stirred at room temperature for 5 hrs. To the reaction solution was added monoethyl-malonate magnesium salt (27.1 g, 94.7 mmol) was added and the mixture was stirred at 60° C. for 2 hrs. Ethyl acetate (50 ml) and water (50 ml) were added to the reaction solution, and conc. hydrochloric acid was added until the aqueous layer showed acidic pH. The reaction solution was extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give ethyl 3-(4-methoxyphenyl)-3-oxopropionate (37.6 g, 94% w/w,. 92%) as a colorless oil.

1. additionwas added
2. stirringthe mixture was stirred at 60° C. for 2 hrs
3. additionwas added until the aqueous layer
4. extractionThe reaction solution was extracted with ethyl acetate (200 ml×2)
5. washThe extract was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

ORD record

ord-b2b0abb869664c728a6259c4d3e16f07

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2