Sodium Hydroxide → 4-(1-methyl-1H-pyrazol-4-yl)benzoic acid

HRID 1635841Notes

Reaction equation

HRID 1635841 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)[CH:4]=[N:3]1.[Mn]([O-])(=O)(=O)=[O:15].[K+].[OH-:20].[Na+]>>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:20])=[CH:9][CH:8]=2)[CH:4]=[N:3]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 43190701-Methyl-4-(4-methylphenyl)-1H-pyrazole

Product 1

HCID 226054524-(1-methyl-1H-pyrazol-4-yl)benzoic acid

Procedure

A mixture of 1-methyl-4-(4-methylphenyl)-1H-pyrazole (1.70 g), potassium permanganate (9.70 g), and 1 N sodium hydroxide (100 ml) was refluxed for 18 hours. The suspension was filtered through diatomaceous earth and cooled. The aqueous solution was extracted with dichloromethane which was discarded. The aqueous solution was acidified to pH 5.5. The resultant precipitate was difficult to filter and was thus extracted with dichloromethane. After evaporation of the solvent, the resulting solid was recrystallized from acetone to yield the title compound (0.60 g), m.p. 274-275° C.; MS m/z: 202 (M)+.

Workup

  1. temperaturewas refluxed for 18 hours
  2. filtrationThe suspension was filtered through diatomaceous earth
  3. temperaturecooled
  4. extractionThe aqueous solution was extracted with dichloromethane which
  5. filtrationto filter
  6. extractionwas thus extracted with dichloromethane
  7. customAfter evaporation of the solvent
  8. customthe resulting solid was recrystallized from acetone

Sources & evidence

ORD record
ord-65be5000f3cf4ec6a0fc736d79467e2e
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

Loading…