Sodium Hydroxide → (+/-)-4-(1-Dodecenyl)-alpha-phenyl-1H-pyrazole-1-acetic acid

HRID 1756950Notes

Reaction equation

HRID 1756950 reaction equation
[OH-].[Na+].[CH:3]([C:15]1[CH:16]=[N:17][N:18]([CH:20]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([O:23]CC)=[O:22])[CH:19]=1)=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(O)C>[CH:3]([C:15]1[CH:16]=[N:17][N:18]([CH:20]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:21]([OH:23])=[O:22])[CH:19]=1)=[CH:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54242059Ethyl (+/-)-4-(1-dodecenyl)-alpha-phenyl-1H-pyrazole-1-acetate

Product 1

HCID 53719716(+/-)-4-(1-Dodecenyl)-alpha-phenyl-1H-pyrazole-1-acetic acidYield 105.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Solid NaOH (6.72 g, 168 mmol) was added to a solution of ethyl (±)-4-(1-dodecenyl)-α-phenyl-1H-pyrazole-1-acetate (44.41 g, 112 mmol) in 500 mL 95% ethanol. The resulting yellow solution was stirred for 1 hour and then concentrated in vacuo. The residue was partitioned between water and ether, the aqueous layer was acidified with concentrated HCl and extracted with ethyl acetate. The ethyl acetate layer was dried over MgSO4, filtered, and concentrated to give a yellow oil (43.4 g) used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water and ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1ee538303bde48de84a6dffb6d206e51
Source dataset
uspto-grants-1995_08
Patent number
US05441975

Reaction notes

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