Hydrochloric Acid → HCID 316818, compound

Aluminum chloride (1.59 g, 11.9 mmol) was added to a dichloromethane (10 mL) solution of phenol (1.03 g, 10.9 mmol) at room temperature, and the mixture was stirred at the same temperature for 45 minutes. Cyclobutanecarboxylic acid chloride (1.33 mL, 11.7 mmol) was added dropwise to the obtained reaction mixture at room temperature, and the mixture was stirred at the same temperature for 4 hours. Further, aluminum chloride (1.58 g, 11.8 mmol) was added at room temperature, and the mixture was stirred. The aluminum chloride was confirmed to be dissolved thoroughly, and then the mixture was stood still overnight. The reaction mixture was added to hydrochloric acid under ice cooling, and the mixture was subjected to extraction once with ethyl acetate. The organic layer thus obtained was washed with brine twice, and then was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10->80:20, v/v) to give the title compound (993 mg, yield: 51%).

1. stirringthe mixture was stirred at the same temperature for 4 hours
2. stirringthe mixture was stirred
3. dissolutionto be dissolved thoroughly
4. waitthe mixture was stood still overnight
5. extractionthe mixture was subjected to extraction once with ethyl acetate
6. customThe organic layer thus obtained
7. washwas washed with brine twice
8. dry with materialwas dried over anhydrous magnesium sulfate
9. distillationThe solvent was distilled off under reduced pressure
10. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10->80:20, v/v)

ORD record

ord-f549680c5dd04f5a8e12bfd6a96b1f43

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722711B2