Sodium Hydroxide → 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylic acid

HRID 1191180Notes

Reaction equation

HRID 1191180 reaction equation
[C:1]([N:5]1[C:9]([CH3:10])=[C:8]([C:11]([O:13]C)=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([N:5]1[C:9]([CH3:10])=[C:8]([C:11]([OH:13])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50853230Methyl 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 222279031-tert-butyl-5-methyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylate in MeOH (20 mL) was treated with 2 M aqueous NaOH solution (7.95 mL, 15.9 mmol) for 48 h at room temperature. The solvent was removed under reduced pressure and the resulting residue was dissolved in H2O (20 mL). The resulting solution was then acidified to pH˜2 using 2 M HCl. The resulting precipitate was isolated by filtration, washed once with H2O (20 mL), and the solid was dried under high vacuum to yield 1-tert-Butyl-5-methyl-1H-pyrazole-4-carboxylic acid. 1H-NMR (400 MHz, d6-DMSO) δ: 12.16 (br. s., 1H), 7.67 (s, 1H), 2.69 (s, 3H), 1.59 (s, 9H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in H2O (20 mL)
  3. customThe resulting precipitate was isolated by filtration
  4. washwashed once with H2O (20 mL)
  5. customthe solid was dried under high vacuum

Sources & evidence

ORD record
ord-5982c95dfc3c442498333e1d14bc51bb
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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