Pyridine → 1-(4-Chloro-2-hydroxy-5-methylphenyl)ethanone

3-Chloro-4-methylphenol (1.00 g) was dissolved in dichloromethane (10 ml) to prepare a solution. Pyridine (747 mg) and acetyl chloride (656 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 trifluoromethanesulfonate (414 mg) was added to the compound thus obtained, and the mixture was suspended in toluene (5 ml) to prepare a suspension which was then 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-chloro-2-hydroxy-5-methyl-phenyl)-ethanone (193 mg, yield 15%).

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 trifluoromethanesulfonate (414 mg) was added to the compound
10. customthus obtained
11. customto prepare a suspension which
12. temperaturewas then heated
13. temperatureunder reflux overnight
14. temperatureThe reaction solution was cooled to room temperature
15. filtrationthe reaction solution was then filtered
16. customThe solvent was removed from the filtrate by distillation under the reduced pressure, water
17. additionwas then added to the residue
18. extractionthe mixture was extracted with ethyl acetate
19. washThe ethyl acetate layer was then washed with water and saturated brine
20. dry with materialwas dried over anhydrous sodium sulfate
21. customThe solvent was removed by distillation under the reduced pressure
22. customthe residue was purified by column chromatography

ORD 기록

ord-2f8100c286b440da9a310d267b3e632a

출처 데이터셋

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07560558B2