Hydrochloric Acid → N-2-(4-Hydroxyphenoxy)ethoxypyrazole

HRID 1588300Notes

Reaction equation

HRID 1588300 reaction equation
Cl.CC(C)([O:5][C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][CH2:12][O:13][N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)=[CH:8][CH:7]=1)C>C(O)C.O>[OH:5][C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][O:13][N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 150188331-[2-(4-tert-Butoxyphenoxy)ethoxy]-1H-pyrazole

Product 1

HCID 15018834N-2-(4-Hydroxyphenoxy)ethoxypyrazoleYield 97%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

9 ml of concentrated hydrochloric acid were added to a solution of 38.4 g (139 mmol) of N-2-[4-(1,1-dimethylethoxy)phenoxy]ethoxypyrazole in 400 ml of ethanol/water (10/1) and the mixture was then refluxed for 8 h. After cooling to RT, the solvent was removed under reduced pressure, the residue was taken up in ethyl acetate, and the solution was washed several times with water. Drying and concentration of the organic phase resulted in 29.6 g (97%) of the required compound as a viscous oil which was employed without further purification in the next stage.

Workup

  1. temperaturethe mixture was then refluxed for 8 h
  2. customthe solvent was removed under reduced pressure
  3. washthe solution was washed several times with water
  4. customDrying

Sources & evidence

ORD record
ord-206cd7ae0c904425b4c6e43172e919aa
Source dataset
uspto-grants-1993_06
Patent number
US05221684

Reaction notes

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