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

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Reaction Steps

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.

Provenance & Evidence