Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexanone | HCID 7967 | — |
| Reactant | 2-Cyclopropyl-6-methylphenol | HCID 22939951 | — |
| Reactant | Sodium 2-cyclopropyl-6-methylphenoxide | HCID 68107637 | — |
| Reactant | HCID 178516198 | HCID 178516198 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 178424441 | HCID 178424441 | 60.2% |
Reaction Steps
To a mixture of 27.4 g (purity: 92.9%; 149 mmol) of sodium 2-cyclopropyl-6-methylphenoxide and 12.5 g of cyclohexanone was added 2.5 g (purity: 98.5%; 14.9 mmol) of 4-hydroxy-3,6-dichloropyridazine at room temperature. Then, the resultant mixture was heated from room temperature to 140° C. to effect a reaction for 7 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and 120 g of pure water and 100 g of toluene were added to the cooled mixture, and stirred for 30 minutes, and an organic phase containing 2-cyclopropyl-6-methylphenol added in an excess amount was separated. Then, the resultant aqueous phase containing a sodium salt of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was quantitatively determined by an HPLC internal standard analysis method, which showed that 2.48 g of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 60.2%) and 16 mg of 3-chloro-6-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 0.4%) were obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08552182B2 |
|---|
| Source dataset | uspto-grants-2013_10 |
|---|
| ORD ID | ord-433ee75bac304daa9c7e56ff73a6cb35 |
|---|
| Source note | uspto-grants-2013_10 |
|---|