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

Temperature

90 °C

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.

1. extractionthe mixture was extracted with ethyl acetate
2. extractionThe organic layer was back-extracted with saturated aqueous sodium hydrogen carbonate solution, and hydrochloric acid
3. additionwas added until the aqueous layer
4. extractionThe reaction mixture was extracted with ethyl acetate
5. washthe extract was washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated under reduced pressure

ORD record

ord-19482a68071343a8991e1380f256298a

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181186B2