Ethanol → Methyl 4-(3-formylphenyl)benzoate

Temperature

100 °C

A solution of tetrakis(triphenylphosphine)palladium (297 mg) was added to a solution of 3-formylphenylboric acid (3.00 g) and methyl 4-bromobenzoic acid (4.30 g) in a mixture of toluene (30 ml), ethanol (50 ml) and saturated aqueous sodium hydrogencarbonate solution (30 ml) at ambient temperature. The mixture was heated at reflux for 2 hours at 100° C. The reaction mixture was partitioned between ethyl acetate and water and the layers were separated. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to afford the title compound (3.37 g) as colorless crystals.

1. temperatureThe mixture was heated
2. customThe reaction mixture was partitioned between ethyl acetate and water
3. customthe layers were separated
4. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was crystallized from diisopropyl ether

ORD record

ord-1bda2d917f2f471eb1211d82bf09e522

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06528525B1