Potassium Carbonate → 1-(2-(Cyclopropylmethoxy)-6-hydroxyphenyl)ethanone

Temperature

50 °C

To a stirred solution of 1-(2,6-dihydroxyphenyl)ethanone (50.0 g, 328 mmol) in acetone (1000 mL) were added potassium carbonate (227 g, 1643 mmol) and (bromomethyl)cyclopropane (35.1 mL, 361 mmol). The mixture was stirred at 50° C. for 2 days. The reaction mixture was filtrated on Celite®, and then the filtrate was concentrated under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The separated organic phase was washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was suspended in hexane. Then the suspension was stirred at 80° C. for 30 min. The solution was filtered and the filtrate was allowed to cool to room temperature. The resulting white solid was collected by filtration, washed with hexane, and dried under reduced pressure to give 1-{2-[(cyclopropylmethyl)oxy]-6-hydroxyphenyl} ethanone as a pale yellow solid (56.3 g, yield; 83%).

1. filtrationThe reaction mixture was filtrated on Celite®
2. concentrationthe filtrate was concentrated under reduced pressure
3. additionThe residue was diluted with water
4. extractionextracted with ethyl acetate
5. washThe separated organic phase was washed with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. stirringThen the suspension was stirred at 80° C. for 30 min
10. filtrationThe solution was filtered
11. temperatureto cool to room temperature
12. filtrationThe resulting white solid was collected by filtration
13. washwashed with hexane
14. customdried under reduced pressure

ORD record

ord-f467e2261411421ab394336a9f33b210

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375103B2