Acetic Acid → Methyl (2-ethyl-4'-hydroxy-1,1'-biphenyl-4-yl)acetate

Temperature

100 °C

Acetic acid (55 ml) and hydrobromic acid (55 ml) were added to (2-ethyl-4′-methoxy-1,1′-biphenyl-4-yl)acetonitrile (5.5 g, 22 mmol) obtained in Example (26-3), and the mixture was stirred at 100° C. for 10 hours. After the reaction mixture was cooled to room temperature, ethyl acetate was added thereto and the mixture was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. After methanol (150 ml) was added to the residue obtained by removing the solvent under reduced pressure, sulfuric acid (3 ml) was added to the mixture under ice-cooling. After the mixture was stirred at room temperature for 1 hour, the solvent was removed under reduced pressure. After ethyl acetate was added to the obtained residue, the mixture was washed with a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1-2/1) to give methyl (2-ethyl-4′-hydroxy-1,1′-biphenyl-4-yl)acetate as a colorless solid (5.0 g, yield: 85%).

1. temperatureAfter the reaction mixture was cooled to room temperature
2. washthe mixture was successively washed with water
3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
4. additionAfter methanol (150 ml) was added to the residue
5. customobtained
6. customby removing the solvent under reduced pressure, sulfuric acid (3 ml)
7. additionwas added to the mixture under ice-
8. temperaturecooling
9. stirringAfter the mixture was stirred at room temperature for 1 hour
10. customthe solvent was removed under reduced pressure
11. additionAfter ethyl acetate was added to the obtained residue
12. washthe mixture was washed with a saturated aqueous NaCl solution
13. dry with materialdried with anhydrous sodium sulfate
14. customThe residue obtained
15. customby removing the solvent under reduced pressure
16. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=5/1-2/1)

ORD record

ord-2fd5a02bc9fb49e8bccc975019bfd490

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923573B2