4-Methoxybenzoic Acid → HCID 21030126, compound

A mixture of 4-methoxybenzoic acid (1.52 g, 10.0 mmol), palladium (II) acetate (0.56 g, 2.5 mmol), copper (II) acetate monohydrate (0.499 g, 2.5 mmol) and 4 Å molecular sieves (1.75 g) in DMF (40 ml) was stirred at room temperature for 5 minutes. Butyl acrylate was add (2.57 g, 20.0 mmol), and the resulting mixture was heated at 120° C. for 25 hours and then at 140° C. for 9 hours. Upon cooling the mixture was filtered and partitioned between dilute HCl aqueous solution and EtOAc. The organic layer was washed with saturated NaHCO3 aqueous solution, water, brine, then dried with anhydrous Na2SO4 and rotary evaporated to a brown oil. The oil was triturated with hexane and the remaining oil was chromatographed through silica gel column (20% to 30% EtOAc/Hexane gradient) to give the desired product contaminated with 4-methoxybenzoic acid. The mixture was dissolved in EtOAc and washed with saturated NaHCO3 aqueous solution, brine, dried with anhydrous Na2SO4. Removal of the solvent yielded butyl (6-methoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetate as a light yellow oil (0.26 g, 9%).

1. temperaturethe resulting mixture was heated at 120° C. for 25 hours
2. waitat 140° C. for 9 hours
3. temperatureUpon cooling the mixture
4. filtrationwas filtered
5. custompartitioned between dilute HCl aqueous solution and EtOAc
6. washThe organic layer was washed with saturated NaHCO3 aqueous solution, water, brine
7. dry with materialdried with anhydrous Na2SO4
8. customrotary evaporated to a brown oil
9. customThe oil was triturated with hexane
10. customthe remaining oil was chromatographed through silica gel column (20% to 30% EtOAc/Hexane gradient)

ORD record

ord-ab72d27dc90942e18b2b51df5990555d

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060844B2