Hydrochloric Acid → 5-[Cyclopropyl(3-hydroxyphenyl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

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Reaction Steps

To a solution of (5-(3-hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (65.0 g) in THF (1.30 L) was added dropwise a 10% solution of cyclopropylmagnesium bromide in THF (2.20 kg) at −11° C. to −1° C. over 1.6 hr, and the mixture was stirred at room temperature for 2 hr. 1N Hydrochloric acid was added to the reaction mixture at 2° C. to 17° C. to adjust the solution to pH 3. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (76.0 g) as a yellow oil.

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