4-Hydroxybenzaldehyde → 2-(4-formylphenoxy)propanoic acid

A solution of ethyl 2-bromopropanoate (6.38 ml, 49.1 mmol), 4-hydroxybenzaldehyde (5.00 g, 40.9 mmol) and potassium carbonate (6.79 g, 49.1 mmol) in acetonitrile (25 ml) was stirred at 60° C. for 16 hrs. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate) to give an oil. To a solution of the obtained oil (9.10 g, 40.9 mmol) in ethanol (200 ml) was added 1N aqueous sodium hydroxide solution (61.4 ml), and the mixture was stirred at room temperature for 16 hrs, and concentrated under reduced pressure. Ethyl acetate was added to the obtained residue. The mixture was washed with 1N hydrochloric acid and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained redsidue was powderized with isopropyl ether to give the title compound (5.68 g).

1. washthe mixture was washed with saturated brine
2. dry with materialdried over anhydrous sodium sulfate
3. customThe solvent was evaporated under reduced pressure
4. customthe obtained residue was purified by alumina column chromatography (developing solvent; ethyl acetate)
5. customto give an oil
6. concentrationconcentrated under reduced pressure
7. additionEthyl acetate was added to the obtained residue
8. washThe mixture was washed with 1N hydrochloric acid and saturated brine
9. dry with materialdried over anhydrous sodium sulfate
10. customThe solvent was evaporated under reduced pressure

ORD record

ord-aac153821707468b83e96fbaab9fac5f

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601868B2