Sodium Hydroxide → HCID 10475983, compound

HRID 1031955Notes

Reaction equation

HRID 1031955 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([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])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[C:1]1([C:7]2[CH:8]=[N:9][N:10]([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])[C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10409426HCID 10409426, compound

Product 1

HCID 10475983HCID 10475983, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl [3-[2-(4,5-diphenyl-1H-pyrazol-1-yl)-ethyl)phenoxy]acetate (0.42 g, 1 mmol), 3N NaOH solution (1.0 mL, 3 mmol) and methanol (30 mL) was heated on a steam bath for 15 minutes before being concentrated in vacuo. The residue was diluted with water, 1N HCl solution added until pH=1 and the mixture extracted with CH2Cl2. The combined organic phase was washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in CH2Cl° and diluted with hexanes to furnish [3-[2-(4,5-diphenyl-1H-pyrazole-1-yl)ethyl]phenoxy]acetic acid (0.28 g, 68%) m.p. 133°-138° C.

Workup

  1. temperaturewas heated on a steam bath for 15 minutes
  2. concentrationbefore being concentrated in vacuo
  3. additionThe residue was diluted with water, 1N HCl solution
  4. additionadded until pH=1
  5. extractionthe mixture extracted with CH2Cl2
  6. washThe combined organic phase was washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in CH2Cl°
  10. additiondiluted with hexanes

Sources & evidence

ORD record
ord-010cf2fe61b741feae7d12b92247df79
Source dataset
uspto-grants-1990_09
Patent number
US04956379

Reaction notes

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