Methyl iodide → 2'-Hydroxy-4'-methoxypropiophenone

6.00 g of 2′,4′-dihydroxypropiophenone was dissolved in 70 ml of acetone. Thereafter, 7.09 g of potassium carbonate and 3.03 ml of methyl iodide were successively added to the reaction solution. The reaction solution was then heated to reflux. Approximately 3 hours later, the reaction solution was stood to cool and then filtered. The filtrate was concentrated under a reduced pressure. A saturated sodium chloride solution and ethyl acetate were added to the residue, so as to separate an organic layer. The obtained organic layer was washed with 2 N hydrochloric acid and a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was solidified from hexane-ethyl acetate, so as to obtain 5.64 g of the subject compound. 1H-NMR (CDCl3) δ (ppm): 1.23 (t, J=7.2 Hz, 3H), 2.95 (q, J=7.2 Hz, 2H), 3.83 (s, 3H), 6.40-6.45 (m, 2H), 7.65 (dd, J=1.6 Hz, 8.0 Hz, 1H), 12.8 (s, 1H).

1. temperatureThe reaction solution was then heated to reflux
2. customApproximately 3 hours
3. temperatureto cool
4. filtrationfiltered
5. concentrationThe filtrate was concentrated under a reduced pressure
6. additionA saturated sodium chloride solution and ethyl acetate were added to the residue
7. customso as to separate an organic layer
8. washThe obtained organic layer was washed with 2 N hydrochloric acid
9. dry with materiala saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate
10. customAfter removing the drying agent
11. filtrationby filtration
12. concentrationthe organic layer was concentrated under a reduced pressure

ORD record

ord-960c7f38786941e9982a2744e0c1e361

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538123B2