Cyclohexanone → HCID 178424441, compound

HRID 1039587Notes

Reaction equation

HRID 1039587 reaction equation
[CH:1]1([C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=2[O-:6])[CH2:3][CH2:2]1.[Na+].C1(=O)CCCCC1.[OH:20][C:21]1[CH:26]=[C:25]([Cl:27])[N:24]=[N:23][C:22]=1Cl.C1(C2C=CC=C(C)C=2O)CC1>C1(C)C=CC=CC=1.O>[Cl:27][C:25]1[N:24]=[N:23][C:22]([O:6][C:5]2[C:7]([CH3:11])=[CH:8][CH:9]=[CH:10][C:4]=2[CH:1]2[CH2:3][CH2:2]2)=[C:21]([OH:20])[CH:26]=1

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 229399512-Cyclopropyl-6-methylphenolHCID 68107637Sodium 2-cyclopropyl-6-methylphenoxideHCID 178516198HCID 178516198, compound

Product 1

HCID 178424441HCID 178424441, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

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.

Workup

  1. customa reaction for 7 hours
  2. customAfter completion of the reaction
  3. additionadded in an excess amount
  4. customwas separated
  5. additionThen, the resultant aqueous phase containing a sodium salt of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol

Sources & evidence

ORD record
ord-433ee75bac304daa9c7e56ff73a6cb35
Source dataset
uspto-grants-2013_10
Patent number
US08552182B2

Reaction notes

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