Hydrochloric Acid → 2'-Hydroxy-4'-methoxy-5'-(3-methyl-2-butenyl)acetophenone

49.2 g of 4′-methoxy-2′-(3-methyl-2-butenyl)oxyacetophenone was dissolved in 100 ml of N,N-diethylaniline. The reaction solution was heated to reflux under nitrogen atmosphere. 3 hours later, the reaction solution was stood to cool, and then, 5 N hydrochloric acid (300 ml) and t-butylmethyl ether (1,000 ml) were added thereto, so as to separate an organic layer. The obtained organic layer was washed with 5 N hydrochloric acid (300 ml×2) and a saturated sodium chloride solution (500 ml), and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, and the residue was then purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain the subject compound. The reaction was further carried out using 4′-methoxy-2′-(3-methyl-2-butenyl)oxyacetophenone (49.0 g) under the above described conditions. The total amount of the subject compounds was 74.1 g.

1. temperatureThe reaction solution was heated
2. temperatureto reflux under nitrogen atmosphere
3. custom3 hours
4. temperatureto cool
5. customso as to separate an organic layer
6. washThe obtained organic layer was washed with 5 N hydrochloric acid (300 ml×2)
7. dry with materiala saturated sodium chloride solution (500 ml), and then dried over anhydrous magnesium sulfate
8. customAfter removing the drying agent
9. filtrationby filtration
10. concentrationthe organic layer was concentrated under a reduced pressure
11. customthe residue was then purified by silica gel column chromatography (hexane/ethyl acetate)
12. customso as to obtain the subject compound

ORD record

ord-6bc46caf5dcd4d939fed4d630ec82556

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538123B2