Sodium Hydroxide → 3-(4-(Methoxycarbonyl)phenyl)propanoic acid

To a solution of methyl 4-(3-methoxy-3-oxopropyl)benzoate (5.05 g, 22.7 mmol) in methanol (120 ml) was added 1N aqueous sodium hydroxide solution (22.7 ml) at 0° C., and the mixture was stirred at room temperature for 16 hrs. After the reaction mixture was concentrated, the residue was dissolved in water, and the solution was washed with diethyl ether. To the aqueous layer was added 6N hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was dissolved in chloroform, and insoluble materials were filtered off. The solvent was evaporated under reduced pressure, and the obtained residue was powderized with hexane to give the title compound (3.61 g) as a powder.

1. concentrationAfter the reaction mixture was concentrated
2. dissolutionthe residue was dissolved in water
3. washthe solution was washed with diethyl ether
4. additionTo the aqueous layer was added 6N hydrochloric acid
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationThe solvent was concentrated under reduced pressure
9. dissolutionthe obtained residue was dissolved in chloroform
10. filtrationinsoluble materials were filtered off
11. customThe solvent was evaporated under reduced pressure

ORD record

ord-0acaf0ebf45c48829690dbe0f61ebfba

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601868B2