Pyridine → HCID 23078451, compound

3-Tert-butyl-4-methoxyphenol (1.00 g) was dissolved in dichloromethane (10 ml) to prepare a solution. Pyridine (658 mg) and acetyl chloride (599 mg) were added to the solution, and the mixture was stirred at room temperature overnight. The solvent was removed by distillation under the reduced pressure, water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous magnesium sulfate, and the solvent was then removed by distillation under the reduced pressure. The residue was dried under the reduced pressure. Scandium trifluoromethane sulfonate (327 mg) was added to the compound thus obtained, the mixture was suspended in toluene (5 ml), and the suspension was heated under reflux overnight. The reaction solution was cooled to room temperature, and the reaction solution was then filtered. The solvent was removed from the filtrate by distillation under the reduced pressure, water was then added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give 1-(4-tert-butyl-2-hydroxy-5-methoxy-phenyl)-ethanone (30 mg, yield 5%).

1. customto prepare a solution
2. customThe solvent was removed by distillation under the reduced pressure, water
3. additionwas then added to the residue
4. extractionthe mixture was extracted with chloroform
5. washThe chloroform layer was washed with water
6. dry with materialwas dried over anhydrous magnesium sulfate
7. customthe solvent was then removed by distillation under the reduced pressure
8. customThe residue was dried under the reduced pressure
9. additionScandium trifluoromethane sulfonate (327 mg) was added to the compound
10. customthus obtained
11. temperaturethe suspension was heated
12. temperatureunder reflux overnight
13. temperatureThe reaction solution was cooled to room temperature
14. filtrationthe reaction solution was then filtered
15. customThe solvent was removed from the filtrate by distillation under the reduced pressure, water
16. additionwas then added to the residue
17. extractionthe mixture was extracted with ethyl acetate
18. washThe ethyl acetate layer was then washed with water and saturated brine
19. dry with materialwas dried over anhydrous sodium sulfate
20. customThe solvent was removed by distillation under the reduced pressure
21. customthe residue was purified by column chromatography

ORD record

ord-a9a3c8d3e01d4ef59e992f4c662804b1

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560558B2