Catechol → HCID 13792091, compound

11 g of catechol, 16.8 g of sodium hydrogencarbonate and 9.5 g of monochloroacetone were dissolved in a mixed solvent of 300 ml of water and 100 ml of isopropyl alcohol, and the solution was heated up to 50° to 60° C. and then stirred for 4 hours. Afterward, 50 ml of a 8% aqueous sodium hydroxide solution and 9.3 g of monochloroacetone were further added, followed by stirring at 50° C. for 5 hours. After standing for cooling, insolubles were removed from the solution by filtration, and the resultant filtrate was concentrated until the volume of the solution became about 300 ml, and then extracted with chloroform. The chloroform layer was washed with a dilute aqueous sodium hydroxide solution and then with water. The solvent was distilled off, and the residue was purified through a silica gel column chromatograph (chloroform/hexane=7/3 to chloroform alone in volume ratio), and then recrystallized from ether/hexane, thereby obtaining 7.73 g of crystals of 2-acetonyloxyphenol.

1. temperaturethe solution was heated up to 50° to 60° C.
2. stirringby stirring at 50° C. for 5 hours
3. temperaturefor cooling
4. custominsolubles were removed from the solution by filtration
5. concentrationthe resultant filtrate was concentrated until the volume of the solution
6. extractionextracted with chloroform
7. washThe chloroform layer was washed with a dilute aqueous sodium hydroxide solution
8. distillationThe solvent was distilled off
9. customthe residue was purified through a silica gel column chromatograph (chloroform/hexane=7/3 to chloroform alone in volume ratio), and
10. customthen recrystallized from ether/hexane

ORD record

ord-721ffc14fcc5488485b5e81646ffebbf

Source dataset

uspto-grants-1994_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05332739