Sodium Hydroxide → HCID 15068039, compound

HRID 1031957Notes

Reaction equation

HRID 1031957 reaction equation
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([O:27]C)=[O:26])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([N:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([CH:29]=[CH:30][CH:31]=3)[O:23][CH2:24][C:25]([OH:27])=[O:26])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15068038methyl [3-[2-(1,5-diphenyl-1H-pyrazol-3-yl)ethyl]phenoxy]acetate

Product 1

HCID 15068039HCID 15068039, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl [3-[2-(1,5-diphenyl-1H-pyrazol-3-yl)ethyl]phenoxy]acetate (3.50 g, 8.5 mmol), 5N NaOH solution (5 mL, 25 mmol) and methanol (70 mL) was heated to reflux on a steam bath for 15 minutes. The solvent was evaporated, the residue diluted with water and acidified with 2N HCl to pH=1. A white solid was filtered off and recrystallized from a mixture of hexanes and CH2Cl2 to give [3-[2-(1,5-diphenyl-1H-pyrazol-3-yl)ethyl]phenoxy]acetic acid (2.85 g, 84%), mp 125°-127° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux on a steam bath for 15 minutes
  3. customThe solvent was evaporated
  4. additionthe residue diluted with water
  5. filtrationA white solid was filtered off
  6. customrecrystallized from a mixture of hexanes and CH2Cl2

Sources & evidence

ORD record
ord-1b03c899fbd14282adc5e9a2f9f4b33d
Source dataset
uspto-grants-1990_09
Patent number
US04956379

Reaction notes

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