Sodium Hydroxide → trimethyl-1H-pyrazol-4-ol

HRID 534100Notes

Reaction equation

HRID 534100 reaction equation
C([O:9][C:10]1[C:11]([CH3:17])=[N:12][N:13]([CH3:16])[C:14]=1[CH3:15])(=O)C1C=CC=CC=1.[OH-].[Na+]>C(O)C>[CH3:16][N:13]1[C:14]([CH3:15])=[C:10]([OH:9])[C:11]([CH3:17])=[N:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 674866031,3,5-trimethyl-1H-pyrazol-4-yl benzoate

Product 1

HCID 12498505trimethyl-1H-pyrazol-4-olYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask was charged with 1,3,5-trimethyl-1H-pyrazol-4-yl benzoate (80 g, 347 mmol), and 500 mL ethanol was added. 3M NaOH (174 ml, 521 mmol) was added and the reaction was stirred at ambient temperature for 2 hours. The ethanol was removed in vacuo and the aqueous layer was extracted with dichloromethane, ethyl acetate and dichloromethane:isopropyl alcohol (4:1). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford 1,3,5-trimethyl-1H-pyrazol-4-ol (34 g, 78% yield) as white solid.

Workup

  1. additionwas added
  2. customThe ethanol was removed in vacuo
  3. extractionthe aqueous layer was extracted with dichloromethane, ethyl acetate and dichloromethane:isopropyl alcohol (4:1)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-38b5115764cc462e913c68cba87ee3ef
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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