Water → 2-(3,5-Dimethyl-1h-pyrazol-1-yl)phenol

HRID 337328Notes

Reaction equation

HRID 337328 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[N:10]1.O.[OH-].[Na+]>C(Cl)Cl>[CH3:15][C:11]1[CH:12]=[C:13]([CH3:14])[N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[OH:2])[N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 181772901-(2-Methoxyphenyl)-3,5-dimethyl-1H-pyrazole

Product 1

HCID 7615532-(3,5-Dimethyl-1h-pyrazol-1-yl)phenolYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.88 g of 1-(2-methoxyphenyl)-3,5-dimethyl-1H-pyrazol was dissolved in 40 ml of methylene chloride, and 32 ml of 1 M solution of borontribromide in methylene chloride was added and stirred at room temperature for 1.5 hours. The reaction mixture was added to 150 ml of water, neutralized with 1N-sodium hydroxide and extracted with 150 ml of ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to yield 2.83 g of the title compound.

Workup

  1. extractionextracted with 150 ml of ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. custompurified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-1a433ad420af43928520f3b7727a72cb
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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