Water → 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-(cyclopropyl(3-hydroxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (164 g) in DMF (1.64 L) was added water (164 mL), and the mixture was stirred at 90° C. for 7 hr. Water and sodium chloride were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was back-extracted with saturated aqueous sodium hydrogen carbonate solution, and hydrochloric acid was added until the aqueous layer became pH 4. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (100 g) as a brown oil. This compound was used for the next step without further purification.

Provenance & Evidence