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

HRID 534089Notes

Reaction equation

HRID 534089 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 added 500 mL ethanol. 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 dichlorormethane: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. customThe ethanol was removed in vacuo
  2. extractionthe aqueous layer was extracted with dichloromethane, ethyl acetate and dichlorormethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b5285ad1f2c4e92ba8a37f35fa4aee8
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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