1-Octanol → HCID 178424441, compound

HRID 1039580Notes

Reaction equation

HRID 1039580 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+].C(O)CCCCCCC.[OH:22][C:23]1[CH:28]=[C:27]([Cl:29])[N:26]=[N:25][C:24]=1Cl.C1(C2C=CC=C(C)C=2O)CC1>C1(C)C=CC=CC=1.O>[Cl:29][C:27]1[N:26]=[N:25][C:24]([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:23]([OH:22])[CH:28]=1

Participants

7

Reactant 4

HCID 9571-OctanolHCID 229399512-Cyclopropyl-6-methylphenolHCID 68107637Sodium 2-cyclopropyl-6-methylphenoxideHCID 178516198HCID 178516198, compound

Product 1

HCID 178424441HCID 178424441, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 25.0 g (147 mmol) of sodium 2-cyclopropyl-6-methylphenoxide and 12.5 g of 1-octanol was added 2.5 g (purity: 98.5%; 14.7 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 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and 80.0 g of pure water and 90.0 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 2.81 g of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 69.2%) and 8.0 mg of 3-chloro-6-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (yield: 0.2%) were obtained.

Workup

  1. customa reaction for 2 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-2aab9331c7a9428fbd7a295d2a0ed49d
Source dataset
uspto-grants-2013_10
Patent number
US08552182B2

Reaction notes

Loading…