Dimethylformamide → Methyl 3-(4-methoxyphenyl)propanoate

3-(4-Hydroxyphenyl)propionic acid (1.36 g, 8.18 mmol) and methyl iodide (1.20 ml, 19.3 mmol) were dissolved in N,N-dimethylformamide (20 ml) and potassium carbonate (3.40 g, 24.6 mmol) was added. The mixture was stirred at 50°-60° C. for 4 hours and at room temperature for 14 hours. The reaction mixture was filtrated and the filtarate was added to saturated brine (100 ml) and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. After filtration, low boiling matters were distilled away from the filtrate under reduced pressure and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give 1.35 g of methyl 3-(4-methoxyphenyl)propionate as a colorless solid (85%). This solid (1.30 g, 6.69 mmol) was dissolved in tetrahydrofuran (10 ml) and a 1N aqueous sodium hydroxide solution (7.0 ml, 7.0 mmol) was added. The mixture was stirred at room temperature for 2 hours. 1N Hydrochloric acid was added to the reaction mixture to adjust its pH to 2-3, and the resulting precipitate was collected by filtration and washed with water to give 1.11 g of 3-((4-methoxyphenyl)propionic acid as a colorless solid (92%).

1. filtrationThe reaction mixture was filtrated
2. additionthe filtarate was added to saturated brine (100 ml)
3. extractionextracted with ethyl acetate
4. dry with materialThe extract was dried over anhydrous magnesium sulfate
5. filtrationAfter filtration, low boiling matters
6. distillationwere distilled away from the filtrate under reduced pressure
7. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

ORD record

ord-2790ada35b4542f48e151338d7d6a093

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753670