تفاعل #598164

معادلة التفاعل

4-chloro-3-methyl-phenol

propionyl chloride

aluminum trichloride

→

1-(5-chloro-2-hydroxy-4-methylphenyl)propan-1-one

المردود 60.0%

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction was concentrated in vacuo
2. 2
   أخرىto remove excess propionyl chloride
3. 3
   أخرىto give an oil
4. 4
   درجة الحرارةthe mixture was heated at 180° C. for 30 minutes
5. 5
   درجة الحرارةThe reaction mixture was then cooled to room temperature
6. 6
   أخرىslowly quenched with 1 N HCl
7. 7
   درجة الحرارةwhile cooling in an ice bath
8. 8
   أخرىThe reaction was partitioned between EtOAc and water
9. 9
   غسيلThe organic layer was washed with 1 N HCl, water, brine
10. 10
    تجفيفdried over magnesium sulfate
11. 11
    تركيزconcentrated
12. 12
    أخرىto give the crude product as a dark oil
13. 13
    أخرىThe product was purified by chromatography on silica gel eluting with hexane

الإجراء التجريبي

The 4-chloro-3-methyl-phenol (2 g, 10 mmol) and the propionyl chloride (1.8 mL, 20. mmol) were combined and the mixture was heated at 60° C. for 2 hours. The reaction was concentrated in vacuo to remove excess propionyl chloride to give an oil. To this was added aluminum trichloride (2.7 g, 20. mmol) and the mixture was heated at 180° C. for 30 minutes. The reaction mixture was then cooled to room temperature and slowly quenched with 1 N HCl while cooling in an ice bath. The reaction was partitioned between EtOAc and water. The organic layer was washed with 1 N HCl, water, brine, dried over magnesium sulfate and concentrated to give the crude product as a dark oil. The product was purified by chromatography on silica gel eluting with hexane:EtOAc gradient to give 1-(5-chloro-2-hydroxy-4-methylphenyl)propan-1-one as a solid (1.5 g, 60%). LCMS calculated for C10H12ClO2 (M+H)+: m/z=199.0. found: 198.9.

المصدر