Potassium Hydroxide → 2-(3,5-Dimethyl-1H-pyrazol-1-yl)benzene-1,3-diol

HRID 337344Notes

Reaction equation

HRID 337344 reaction equation
CC1C=CC(S([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:13]=2[N:19]2[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[N:20]2)(=O)=O)=CC=1.[OH-].[K+]>C(O)C.O>[CH3:25][C:21]1[CH:22]=[C:23]([CH3:24])[N:19]([C:13]2[C:14]([OH:18])=[CH:15][CH:16]=[CH:17][C:12]=2[OH:11])[N:20]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 867032542-(3,5-Dimethyl-1H-pyrazol-1-yl)-3-hydroxyphenyl 4-methylbenzenesulfonate

Product 1

HCID 601438812-(3,5-Dimethyl-1H-pyrazol-1-yl)benzene-1,3-diolYield 58.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To 62 mg of 2-(3,5-dimethyl-1H-pyrazol-1-yl)-3-hydroxyphenyl 4-methylbenzene sulfonate was added a solution in which 97 mg of potassium hydroxide was dissolved in 1.5 ml of ethanol and 1.5 ml of water, and heated at reflux for 3.5 hours. To the reaction mixture, 20 ml of water was added, and extracted with 20 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified using preparative thin-layer silica gel column chromatography (hexane:ethyl acetate=1:1) to yield 20.8 mg of the title compound.

Workup

  1. temperatureat reflux for 3.5 hours
  2. extractionextracted with 20 ml of ethyl acetate
  3. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. custompurified

Sources & evidence

ORD record
ord-85206d9f8af0439a8851e6e3c895e74a
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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