Sodium Hydroxide → HCID 67793757, compound

HRID 1460698Notes

Reaction equation

HRID 1460698 reaction equation
[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO>[OH2:32].[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19982284HCID 19982284, compound

Product 1

HCID 67793757HCID 67793757, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 3,4,5-triphenyl-1H-pyrazol-1-octanoate (3 g, 6.4 mmol), 3N aqueous sodium hydroxide solution (6.4 mL, 19 mmol) and methanol (40 mL) was heated on a steam bath for 25 minutes before being cooled and concentrated in vacuo. The residue was diluted with water (25 mL) and 2N hydrochloric acid solution added until pH=1. The mixture was extracted with dichloromethane and the combined extracts washed with water and saturated NaCl solution before being dried over sodium sulfate. Removal of the solvent left an oil that slowly crystallized. Recrystallization from a mixture of hexane and dichloromethane (2:1) afforded 3,4,5-triphenyl-1H-pyrazol-1-octanoic acid hydrate (1.19 g, 42%); m.p.=97.5°-99.5° C. MS(CI): m/e=439 (MH+).

Workup

  1. temperaturewas heated on a steam bath for 25 minutes
  2. temperaturebefore being cooled
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with water (25 mL) and 2N hydrochloric acid solution
  5. additionadded until pH=1
  6. extractionThe mixture was extracted with dichloromethane
  7. washthe combined extracts washed with water and saturated NaCl solution
  8. dry with materialbefore being dried over sodium sulfate
  9. customRemoval of the solvent
  10. waitleft an oil that
  11. customslowly crystallized
  12. customRecrystallization
  13. additionfrom a mixture of hexane and dichloromethane (2:1)

Sources & evidence

ORD record
ord-2b05b7dac39c4b898719309e9879fd04
Source dataset
uspto-grants-1991_12
Patent number
US05071866

Reaction notes

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