Potassium Carbonate → 3-(cyclopropylMethoxy)benzoic acid

Temperature

70 °C

To a solution of ethyl 3-hydroxybenzoate (15.0 g) in DMF (150 mL) were added potassium carbonate (25.0 g) and (bromomethyl)cyclopropane (13.1 mL), and the mixture was stirred with heating at 70° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate, and washed with saturated brine. The obtained organic layer was subjected to silica gel column chromatography (NH, ethyl acetate), and the solvent was evaporated. To a solution of the obtained residue in a mixed solvent of THF (100 mL) and methanol (50 mL) was added 2 M aqueous sodium hydroxide solution (47 mL), and the mixture was stirred with heating at 60° C. for 40 min. The reaction mixture was allowed to cool to room temperature, and neutralized with 6 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained solid was washed with diethyl ether/hexane to give the title compound (13.4 g).

1. temperatureto cool to room temperature
2. washwashed with saturated brine
3. customthe solvent was evaporated
4. additionTo a solution of the obtained residue in a mixed solvent of THF (100 mL) and methanol (50 mL) was added 2 M aqueous sodium hydroxide solution (47 mL)
5. stirringthe mixture was stirred
6. temperaturewith heating at 60° C. for 40 min
7. temperatureto cool to room temperature
8. extractionthe mixture was extracted with ethyl acetate
9. washThe obtained organic layer was washed with saturated brine
10. dry with materialdried over anhydrous magnesium sulfate
11. customthe solvent was evaporated under reduced pressure
12. washThe obtained solid was washed with diethyl ether/hexane

ORD record

ord-5b8660974edc492c893aa49be2b800dc

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133129B2