Potassium Carbonate → Acetic acid, 2-(2-acetyl-4-methoxyphenoxy)-

To a mixture of 1-(2-hydroxy-5-methoxyphenyl)ethanone (25.0 g), methyl bromoacetate (15.5 mL) and N,N-dimethylformamide (250 mL) was added potassium carbonate (31.1 g), and the mixture was stirred overnight at room temperature. The insoluble material was filtered off, 1N hydrochloric acid was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a brown solid. To a mixture of the obtained solid, tetrahydrofuran (300 mL) and ethanol (300 mL) was added 1N aqueous sodium hydroxide solution (300 mL), and the mixture was stirred overnight at room temperature, and concentrated under reduced pressure. 1N Hydrochloric acid (300 mL) was added to the residue at 0° C., and the resulting precipitate was collected by filtration to give the title object compound (34.2 g, quantitative) as a white solid.

1. filtrationThe insoluble material was filtered off
2. addition1N hydrochloric acid was added to the filtrate
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto give a brown solid
8. stirringthe mixture was stirred overnight at room temperature
9. concentrationconcentrated under reduced pressure
10. addition1N Hydrochloric acid (300 mL) was added to the residue at 0° C.
11. filtrationthe resulting precipitate was collected by filtration
12. customto give the title object compound (34.2 g, quantitative) as a white solid

ORD record

ord-a48619a13d034998aa4c0e0937fc3fd3

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2