Hydrochloric Acid → HCID 178516201, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 25.0 g (266 mmol) of phenol and 30.0 g of cyclohexanol was charged, and 25.5 g (266 mmol) of sodium t-butoxide was added to the mixture over one hour, and then stirred at 70° C. for 30 minutes. The resultant solution was cooled to 40° C., and then 8.94 g (purity: 98%; 153.1 mmol) of 4-hydroxy-3,6-dichloropyridazine was added to the cooled solution. Then, the resultant mixture was heated from 40° C. to 140° C. to effect a reaction for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and 100 g of pure water and 100 g of toluene were added to the cooled mixture, and stirred for 30 minutes. Then, 41.7 g (400 mmol) of a 35% aqueous hydrochloric acid solution was added dropwise to the resultant mixture, and an organic phase containing phenol added in an excess amount was separated. 287 g of toluene was added to the resultant aqueous phase, and stirred at room temperature for 30 minutes, and then an organic phase was separated. Then, the resultant aqueous phase containing a sodium salt of 6-chloro-3-phenoxy-4-pyridazinol was added dropwise to a 35% aqueous hydrochloric acid solution at 0° C. to deposit solids, followed by filtration. The resultant solids were washed with pure water and dried under a reduced pressure, and dissolved in an organic solvent and quantitatively determined by an HPLC area percentage method, which showed that 9.94 g of 6-chloro-3-phenoxy-4-pyridazinol (yield: 84.0%) was obtained.

Provenance & Evidence