Water → HCID 23143847, compound

3-Methoxy-4-phenylbenzaldehyde (23.0 g) was dissolved in dichloromethane (150 mL). To the stirred mixture was added dropwise boron tribromide (15.4 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. To the stirred reaction mixture was added dropwise water (20 mL) under ice-cooling, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was suspended in methanol (100 mL) and 2 mol/L hydrochloric acid (50 mL), and the mixture was stirred at 50° C. for 2 hours. To the reaction mixture was added brine, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (13.8 g).

1. temperaturecooling
2. customTo the stirred reaction mixture
3. temperaturecooling
4. extractionthe resulting mixture was extracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was removed under reduced pressure
8. stirring2 mol/L hydrochloric acid (50 mL), and the mixture was stirred at 50° C. for 2 hours
9. additionTo the reaction mixture was added brine
10. extractionthe resulting mixture was extracted with ethyl acetate
11. washThe organic layer was washed with brine
12. dry with materialdried over anhydrous magnesium sulfate
13. customThe solvent was removed under reduced pressure
14. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

ORD record

ord-37e4149d337042e4adca5b041c8e9c58

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547680B2