O-Cresol → HCID 23013956, compound

HRID 1821678Notes

Reaction equation

HRID 1821678 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Na].[Cl:10][C:11]1[N:12]=[N:13][C:14](Cl)=[C:15]([O:18][CH3:19])[C:16]=1Cl>C1(C)C=CC=CC=1>[Cl:10][C:11]1[N:12]=[N:13][C:14]([O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])=[C:15]([O:18][CH3:19])[C:16]=1[O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 335O-CresolHCID 5360545SodiumHCID 229399153,4,6-Trichloro-5-methoxypyridazine

Product 1

HCID 23013956HCID 23013956, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In toluene (100 mL) was dissolved 5.32 g (49.3 mmol) of 2-methylphenol, and 1.13 g (49.1 mmol) of sodium, and then, 5.80 g (27.2 mmol) of 3,4,6-trichloro-5-methoxypyridazine were added to the solution and the resulting mixture was stirred for 4 hours under reflux. The reaction mixture was poured into ice-cold water, and extracted with ethyl acetate. The organic layers were combined, washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, gradient) and recrystallized from isopropyl ether to obtain 3.0 g (8.4 mmol, Yield: 31%) of 3-chloro-5-methoxy-4,6-bis(2-methylphenoxy)pyridazine.

Workup

  1. temperatureunder reflux
  2. additionThe reaction mixture was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate, gradient)
  8. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-be2dfb9eb73e4f8e8fe0914fefd18a55
Source dataset
uspto-grants-2009_10
Patent number
US07608563B2

Reaction notes

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