1-Chloro-3-methyl-2-butene → Ethanone, 1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-

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Reaction Steps

In tetrahydrofuran were dissolved and suspended 66.5 g of 2',4',6'-trihydroxyacetophenone and 173.0 g of potassium carbonate, and 56.0 ml of 1-chloro-3-methyl-2-butene was dropped into the solution. The mixture was stirred at room temperature for 2 hours and extracted with dimethyl ether, and the organic layer was washed with a 5% solution of potassium carbonate and then with water. The organic layer was shaken with a saturated solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under a reduced pressure. Recrystallization from benzene gave 31.8 g (yield=34.0%) of 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone.

Provenance & Evidence