O-Cresol → HCID 13321722, compound

HRID 1821654Notes

Reaction equation

HRID 1821654 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][CH:7]=1.[CH3:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[OH:16].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([O:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 335O-CresolHCID 11430Potassium CarbonateHCID 673313,6-Dichloropyridazine

Product 1

HCID 13321722HCID 13321722, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 278.7 g (1.87 mol) of 3,6-dichloropyridazine, 202.3 g (1.87 mol) of 2-methylphenol and 259 g (1.87 mol) of potassium carbonate was stirred at 160° C. for 6 hours. The reaction mixture was cooled to 70° C. and 2 L of ethyl acetate was added. This mixture was washed successively with 1 mol/L sodium hydroxide aqueous solution (4×500 mL), water (4×500 mL) and brine (50 mL), and dried over anhydrous magnesium sulfate. The solvent was removed, and isopropyl ether was added to the residue to form crystal. The crystal was collected by filtration to obtain 234.2 g (1.06 mol, Yield: 56.7%) of 3-chloro-6-(2-methylphenoxy)pyridazine.

Workup

  1. temperatureThe reaction mixture was cooled to 70° C.
  2. washThis mixture was washed successively with 1 mol/L sodium hydroxide aqueous solution (4×500 mL), water (4×500 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed
  5. additionisopropyl ether was added to the residue
  6. customto form crystal
  7. filtrationThe crystal was collected by filtration

Sources & evidence

ORD record
ord-fc4478db709d44bc90c3b413a5bb51c9
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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